Phenyl Amide Compounds - Enigen Science Publishing

phenyl acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of acetyl chloride ( 15.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of propanoyl chloride ( 18.5 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl cyclopropanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclopropanecarbonyl chloride ( 20.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl butanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of butanoyl chloride ( 21.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-methylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methylpropanoyl chloride ( 21.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl methoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of methoxyacetyl chloride ( 21.7 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl chloroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of chloroacetyl chloride ( 22.58 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-pentenamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-pentenoyl chloride ( 23.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl cyclobutanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclobutanecarbonyl chloride ( 23.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl pentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentanoyl chloride ( 24.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-methylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methylbutanoyl chloride ( 24.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-chloropropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloropropanoyl chloride ( 25.39 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl furan-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-furoyl chloride ( 26.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-isoxazolecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-isoxazolecarbonyl chloride ( 26.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl trifluoroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of trifluoroacetyl chloride ( 26.49 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl cyclopentanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclopentanecarbonyl chloride ( 26.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl hexanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of hexanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,3-dimethylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,3-dimethylbutanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-ethylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-ethylbutanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of benzoyl chloride ( 28.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-chlorobutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-chlorobutanoyl chloride ( 28.19 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-methylfuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methyl-2-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-methylfuran-3-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methyl-3-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-methylfuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-methyl-2-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-thiophenecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-thiophenecarbonyl chloride ( 29.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl cyclohexanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclohexanecarbonyl chloride ( 29.32 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl heptanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of heptanoyl chloride ( 29.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(methoxycarbonyl)propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(methoxycarbonyl)propanoyl chloride ( 30.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl phenylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of phenylacetyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-chloropentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-chloropentanoyl chloride ( 31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl bromoacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of bromoacetyl chloride ( 31.47 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluorobenzoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-fluorobenzoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluorobenzoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,5-dimethylfuran-3-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-dimethyl-3-furoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-methyl-2-thiophenecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methyl-2-thiophenecarbonyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-methyl-2-thiophenecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methyl-2-thiophenecarbonyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-thienylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-thienylacetyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-cyclopentylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-cyclopentylpropanoyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl cyclohexylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclohexylacetyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl octanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of octanoyl chloride ( 32.53 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(ethoxycarbonyl)propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(ethoxycarbonyl)propanoyl chloride ( 32.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(methoxycarbonyl)butanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(methoxycarbonyl)butanoyl chloride ( 32.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-cyanobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-cyanobenzoyl chloride ( 33.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-cyanobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-cyanobenzoyl chloride ( 33.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-ethylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-ethylbenzoyl chloride ( 33.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-phenylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-phenylpropanoyl chloride ( 33.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 6-chlorohexanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-chlorohexanoyl chloride ( 33.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methoxybenzoyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methoxybenzoyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methoxybenzoyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl phenoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of phenoxyacetyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-bromopropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-bromopropanoyl chloride ( 34.28 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-fluoro-2-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-fluoro-2-methylbenzoyl chloride ( 34.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-fluoro-3-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluoro-3-methylbenzoyl chloride ( 34.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (4-fluorophenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-fluorophenyl)acetyl chloride ( 34.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-chlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-chlorobenzoyl chloride ( 35 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-chlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chlorobenzoyl chloride ( 35 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-chlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-chlorobenzoyl chloride ( 35 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-nitrofuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-nitro-2-furoyl chloride ( 35.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-chloronicotinamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-chloronicotinoyl chloride ( 35.2 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 6-chloronicotinamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-chloronicotinoyl chloride ( 35.2 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,5-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,6-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,6-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,4-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,3-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,3-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,5-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,4-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl nonanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of nonanoyl chloride ( 35.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(ethoxycarbonyl)butanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(ethoxycarbonyl)butanoyl chloride ( 35.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-(methoxycarbonyl)pentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-(methoxycarbonyl)pentanoyl chloride ( 35.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 1-benzofuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1-benzofuran-2-carbonyl chloride ( 36.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (1R,2R)-2-phenylcyclopropanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (1R,2R)-2-phenylcyclopropanecarbonyl chloride ( 36.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl trichloroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of trichloroacetyl chloride ( 36.36 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-propylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-propylbenzoyl chloride ( 36.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 1,3-benzodioxole-5-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1,3-benzodioxole-5-carbonyl chloride ( 36.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-ethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-ethoxybenzoyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-ethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-ethoxybenzoyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (3-methoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (3-methoxyphenyl)acetyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (4-methoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-methoxyphenyl)acetyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (benzyloxy)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (benzyloxy)acetyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-bromobutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-bromobutanoyl chloride ( 37.08 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-nitrobenzoyl chloride ( 37.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-nitrobenzoyl chloride ( 37.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-nitrobenzoyl chloride ( 37.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(methylsulfanyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(methylsulfanyl)benzoyl chloride ( 37.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (phenylsulfanyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (phenylsulfanyl)acetyl chloride ( 37.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (6E)-8-methyl-6-nonenamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (6E)-8-methyl-6-nonenoyl chloride ( 37.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(chloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(chloromethyl)benzoyl chloride ( 37.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(chloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(chloromethyl)benzoyl chloride ( 37.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (4-chlorophenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-chlorophenyl)acetyl chloride ( 37.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,6-difluoro-3-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,6-difluoro-3-methylbenzoyl chloride ( 38.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 1-naphthamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1-naphthoyl chloride ( 38.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-naphthamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-naphthoyl chloride ( 38.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl decanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of decanoyl chloride ( 38.14 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-quinolinecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-quinolinecarbonyl chloride ( 38.32 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-quinoxalinecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-quinoxalinecarbonyl chloride ( 38.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-chloro-2-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-chloro-2-fluorobenzoyl chloride ( 38.6 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-chloro-2-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloro-2-fluorobenzoyl chloride ( 38.6 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,3,6-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,3,6-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,3,4-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,3,4-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,4,5-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4,5-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,4,5-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4,5-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-methyl-1-benzofuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methyl-1-benzofuran-2-carbonyl chloride ( 38.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl benzo(B)thiophene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of benzo(B)thiophene-2-carbonyl chloride ( 39.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-butylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-butylbenzoyl chloride ( 39.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-tert-butylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-tert-butylbenzoyl chloride ( 39.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-(acetyloxy)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-(acetyloxy)benzoyl chloride ( 39.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-bromopentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-bromopentanoyl chloride ( 39.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-methyl-3-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methyl-3-nitrobenzoyl chloride ( 39.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,4-dimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4-dimethoxybenzoyl chloride ( 40.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,5-dimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-dimethoxybenzoyl chloride ( 40.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,4-dimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-dimethoxybenzoyl chloride ( 40.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 10-undecenamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 10-undecenoyl chloride ( 40.54 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl undecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of undecanoyl chloride ( 40.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (4-chlorophenoxy)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-chlorophenoxy)acetyl chloride ( 41 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 7-(methoxycarbonyl)heptanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 7-(methoxycarbonyl)heptanoyl chloride ( 41.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-(trifluoromethyl)benzoyl chloride ( 41.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(trifluoromethyl)benzoyl chloride ( 41.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(trifluoromethyl)benzoyl chloride ( 41.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,4-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,4-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,6-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,6-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,5-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 6-(trifluoromethyl)nicotinamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-(trifluoromethyl)nicotinoyl chloride ( 41.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carbonyl chloride ( 42.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-pentylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-pentylbenzoyl chloride ( 42.13 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-butoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-butoxybenzoyl chloride ( 42.53 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 6-bromohexanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-bromohexanoyl chloride ( 42.7 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (2,5-dimethoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2,5-dimethoxyphenyl)acetyl chloride ( 42.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (3,4-dimethoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (3,4-dimethoxyphenyl)acetyl chloride ( 42.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl biphenyl-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of biphenyl-4-carbonyl chloride ( 43.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl dodecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of dodecanoyl chloride ( 43.75 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-bromobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-bromobenzoyl chloride ( 43.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-bromobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-bromobenzoyl chloride ( 43.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-bromobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-bromobenzoyl chloride ( 43.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-chloro-3-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-chloro-3-nitrobenzoyl chloride ( 44 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(dichloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(dichloromethyl)benzoyl chloride ( 44.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(dichloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(dichloromethyl)benzoyl chloride ( 44.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(trifluoromethoxy)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(trifluoromethoxy)benzoyl chloride ( 44.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,4,5-trifluoro-3-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4,5-trifluoro-3-methoxybenzoyl chloride ( 44.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-hexylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-hexylbenzoyl chloride ( 44.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-fluoro-4-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-fluoro-4-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-fluoro-4-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-4-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-fluoro-3-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluoro-3-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-fluoro-3-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-3-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-fluoro-5-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-fluoro-5-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-fluoro-6-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-6-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-fluoro-2-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluoro-2-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-fluoro-5-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-5-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-fluoro-2-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-fluoro-2-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,4-dichloro-5-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-dichloro-5-fluorobenzoyl chloride ( 45.48 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,5-diethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-diethoxybenzoyl chloride ( 45.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,5-diethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-diethoxybenzoyl chloride ( 45.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,5-dinitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-dinitrobenzoyl chloride ( 46.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,4,5-trimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4,5-trimethoxybenzoyl chloride ( 46.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl diphenylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of diphenylacetyl chloride ( 46.13 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-chloro-1-benzothiophene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloro-1-benzothiophene-2-carbonyl chloride ( 46.21 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (-)-menthoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (-)-menthoxyacetyl chloride ( 46.54 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl tridecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of tridecanoyl chloride ( 46.55 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-bromomethyl-benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-bromomethyl-benzoyl chloride ( 46.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (2-bromophenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2-bromophenyl)acetyl chloride ( 46.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 9-(methoxycarbonyl)nonanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 9-(methoxycarbonyl)nonanoyl chloride ( 46.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-heptylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-heptylbenzoyl chloride ( 47.75 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-[(trifluoromethyl)sulfanyl]benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-[(trifluoromethyl)sulfanyl]benzoyl chloride ( 48.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-(hexyloxy)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(hexyloxy)benzoyl chloride ( 48.14 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 9-oxo-9H-fluorene-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 9-oxo-9H-fluorene-4-carbonyl chloride ( 48.53 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,4,6-trichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4,6-trichlorobenzoyl chloride ( 48.78 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl tetradecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of tetradecanoyl chloride ( 49.36 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-chloro-6-fluoro-1-benzothiophene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloro-6-fluoro-1-benzothiophene-2-carbonyl chloride ( 49.81 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-bromo-2-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-bromo-2-methoxybenzoyl chloride ( 49.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride ( 50.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride ( 50.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarbonyl chloride ( 51.21 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-oxo-3H-benzo[f]chromene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-oxo-3H-benzo[f]chromene-2-carbonyl chloride ( 51.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl pentafluorophenoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentafluorophenoxyacetyl chloride ( 52.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl pentadecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentadecanoyl chloride ( 52.16 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl pentachloropropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentachloropropionyl chloride ( 52.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl chloro(diphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of chloro(diphenyl)acetyl chloride ( 53.02 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-iodobenzoyl chloride ( 53.29 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 4-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-iodobenzoyl chloride ( 53.29 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride ( 54.81 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-(benzoyloxymethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-(benzoyloxymethyl)benzoyl chloride ( 54.93 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl hexadecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of hexadecanoyl chloride ( 54.97 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,5-bis(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-bis(trifluoromethyl)benzoyl chloride ( 55.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2,5-bis(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-bis(trifluoromethyl)benzoyl chloride ( 55.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 2-fluoro-5-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-5-iodobenzoyl chloride ( 56.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride ( 58.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl (2-bromo-4,5-dimethoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2-bromo-4,5-dimethoxyphenyl)acetyl chloride ( 58.7 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3-benzyloxy-4-methoxy-2-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-benzyloxy-4-methoxy-2-nitrobenzoyl chloride ( 64.34 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 5-bromo-2-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-bromo-2-iodobenzoyl chloride ( 69.07 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 7-chloro-2-(4-chlorophenyl)-6-methyl-4-quinolinecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 7-chloro-2-(4-chlorophenyl)-6-methyl-4-quinolinecarbonyl chloride ( 70.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

phenyl 3,4,5-triiodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 1-aminobenzene ( 18.62 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4,5-triiodobenzoyl chloride ( 103.65 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of acetyl chloride ( 15.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of propanoyl chloride ( 18.5 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl cyclopropanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclopropanecarbonyl chloride ( 20.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl butanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of butanoyl chloride ( 21.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-methylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methylpropanoyl chloride ( 21.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl methoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of methoxyacetyl chloride ( 21.7 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl chloroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of chloroacetyl chloride ( 22.58 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-pentenamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-pentenoyl chloride ( 23.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl cyclobutanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclobutanecarbonyl chloride ( 23.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl pentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentanoyl chloride ( 24.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-methylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methylbutanoyl chloride ( 24.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-chloropropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloropropanoyl chloride ( 25.39 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl furan-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-furoyl chloride ( 26.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-isoxazolecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-isoxazolecarbonyl chloride ( 26.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl trifluoroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of trifluoroacetyl chloride ( 26.49 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl cyclopentanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclopentanecarbonyl chloride ( 26.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl hexanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of hexanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,3-dimethylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,3-dimethylbutanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-ethylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-ethylbutanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of benzoyl chloride ( 28.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-chlorobutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-chlorobutanoyl chloride ( 28.19 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-methylfuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methyl-2-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-methylfuran-3-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methyl-3-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-methylfuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-methyl-2-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-thiophenecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-thiophenecarbonyl chloride ( 29.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl cyclohexanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclohexanecarbonyl chloride ( 29.32 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl heptanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of heptanoyl chloride ( 29.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(methoxycarbonyl)propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(methoxycarbonyl)propanoyl chloride ( 30.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl phenylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of phenylacetyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-chloropentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-chloropentanoyl chloride ( 31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl bromoacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of bromoacetyl chloride ( 31.47 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluorobenzoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-fluorobenzoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluorobenzoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,5-dimethylfuran-3-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-dimethyl-3-furoyl chloride ( 31.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-methyl-2-thiophenecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methyl-2-thiophenecarbonyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-methyl-2-thiophenecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methyl-2-thiophenecarbonyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-thienylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-thienylacetyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-cyclopentylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-cyclopentylpropanoyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl cyclohexylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclohexylacetyl chloride ( 32.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl octanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of octanoyl chloride ( 32.53 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(ethoxycarbonyl)propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(ethoxycarbonyl)propanoyl chloride ( 32.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(methoxycarbonyl)butanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(methoxycarbonyl)butanoyl chloride ( 32.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-cyanobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-cyanobenzoyl chloride ( 33.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-cyanobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-cyanobenzoyl chloride ( 33.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-ethylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-ethylbenzoyl chloride ( 33.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-phenylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-phenylpropanoyl chloride ( 33.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 6-chlorohexanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-chlorohexanoyl chloride ( 33.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methoxybenzoyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methoxybenzoyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methoxybenzoyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl phenoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of phenoxyacetyl chloride ( 34.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-bromopropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-bromopropanoyl chloride ( 34.28 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-fluoro-2-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-fluoro-2-methylbenzoyl chloride ( 34.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-fluoro-3-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluoro-3-methylbenzoyl chloride ( 34.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (4-fluorophenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-fluorophenyl)acetyl chloride ( 34.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-chlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-chlorobenzoyl chloride ( 35 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-chlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chlorobenzoyl chloride ( 35 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-chlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-chlorobenzoyl chloride ( 35 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-nitrofuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-nitro-2-furoyl chloride ( 35.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-chloronicotinamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-chloronicotinoyl chloride ( 35.2 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 6-chloronicotinamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-chloronicotinoyl chloride ( 35.2 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,5-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,6-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,6-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,4-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,3-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,3-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,5-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,4-difluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-difluorobenzoyl chloride ( 35.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl nonanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of nonanoyl chloride ( 35.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(ethoxycarbonyl)butanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(ethoxycarbonyl)butanoyl chloride ( 35.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-(methoxycarbonyl)pentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-(methoxycarbonyl)pentanoyl chloride ( 35.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 1-benzofuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1-benzofuran-2-carbonyl chloride ( 36.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (1R,2R)-2-phenylcyclopropanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (1R,2R)-2-phenylcyclopropanecarbonyl chloride ( 36.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl trichloroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of trichloroacetyl chloride ( 36.36 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-propylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-propylbenzoyl chloride ( 36.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 1,3-benzodioxole-5-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1,3-benzodioxole-5-carbonyl chloride ( 36.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-ethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-ethoxybenzoyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-ethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-ethoxybenzoyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (3-methoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (3-methoxyphenyl)acetyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (4-methoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-methoxyphenyl)acetyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (benzyloxy)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (benzyloxy)acetyl chloride ( 36.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-bromobutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-bromobutanoyl chloride ( 37.08 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-nitrobenzoyl chloride ( 37.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-nitrobenzoyl chloride ( 37.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-nitrobenzoyl chloride ( 37.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(methylsulfanyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(methylsulfanyl)benzoyl chloride ( 37.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (phenylsulfanyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (phenylsulfanyl)acetyl chloride ( 37.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (6E)-8-methyl-6-nonenamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (6E)-8-methyl-6-nonenoyl chloride ( 37.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(chloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(chloromethyl)benzoyl chloride ( 37.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(chloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(chloromethyl)benzoyl chloride ( 37.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (4-chlorophenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-chlorophenyl)acetyl chloride ( 37.8 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,6-difluoro-3-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,6-difluoro-3-methylbenzoyl chloride ( 38.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 1-naphthamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1-naphthoyl chloride ( 38.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-naphthamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-naphthoyl chloride ( 38.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl decanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of decanoyl chloride ( 38.14 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-quinolinecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-quinolinecarbonyl chloride ( 38.32 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-quinoxalinecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-quinoxalinecarbonyl chloride ( 38.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-chloro-2-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-chloro-2-fluorobenzoyl chloride ( 38.6 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-chloro-2-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloro-2-fluorobenzoyl chloride ( 38.6 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,3,6-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,3,6-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,3,4-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,3,4-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,4,5-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4,5-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,4,5-trifluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4,5-trifluorobenzoyl chloride ( 38.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-methyl-1-benzofuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methyl-1-benzofuran-2-carbonyl chloride ( 38.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl benzo(B)thiophene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of benzo(B)thiophene-2-carbonyl chloride ( 39.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-butylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-butylbenzoyl chloride ( 39.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-tert-butylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-tert-butylbenzoyl chloride ( 39.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-(acetyloxy)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-(acetyloxy)benzoyl chloride ( 39.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-bromopentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-bromopentanoyl chloride ( 39.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-methyl-3-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methyl-3-nitrobenzoyl chloride ( 39.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,4-dimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4-dimethoxybenzoyl chloride ( 40.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,5-dimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-dimethoxybenzoyl chloride ( 40.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,4-dimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-dimethoxybenzoyl chloride ( 40.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 10-undecenamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 10-undecenoyl chloride ( 40.54 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl undecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of undecanoyl chloride ( 40.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (4-chlorophenoxy)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (4-chlorophenoxy)acetyl chloride ( 41 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 7-(methoxycarbonyl)heptanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 7-(methoxycarbonyl)heptanoyl chloride ( 41.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-(trifluoromethyl)benzoyl chloride ( 41.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(trifluoromethyl)benzoyl chloride ( 41.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(trifluoromethyl)benzoyl chloride ( 41.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,4-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,4-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,6-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,6-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,5-dichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-dichlorobenzoyl chloride ( 41.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 6-(trifluoromethyl)nicotinamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-(trifluoromethyl)nicotinoyl chloride ( 41.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carbonyl chloride ( 42.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-pentylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-pentylbenzoyl chloride ( 42.13 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-butoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-butoxybenzoyl chloride ( 42.53 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 6-bromohexanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 6-bromohexanoyl chloride ( 42.7 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (2,5-dimethoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2,5-dimethoxyphenyl)acetyl chloride ( 42.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (3,4-dimethoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (3,4-dimethoxyphenyl)acetyl chloride ( 42.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl biphenyl-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of biphenyl-4-carbonyl chloride ( 43.33 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl dodecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of dodecanoyl chloride ( 43.75 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-bromobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-bromobenzoyl chloride ( 43.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-bromobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-bromobenzoyl chloride ( 43.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-bromobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-bromobenzoyl chloride ( 43.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-chloro-3-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-chloro-3-nitrobenzoyl chloride ( 44 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(dichloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(dichloromethyl)benzoyl chloride ( 44.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(dichloromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(dichloromethyl)benzoyl chloride ( 44.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(trifluoromethoxy)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(trifluoromethoxy)benzoyl chloride ( 44.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,4,5-trifluoro-3-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4,5-trifluoro-3-methoxybenzoyl chloride ( 44.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-hexylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-hexylbenzoyl chloride ( 44.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-fluoro-4-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-fluoro-4-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-fluoro-4-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-4-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-fluoro-3-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluoro-3-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-fluoro-3-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-3-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-fluoro-5-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-fluoro-5-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-fluoro-6-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-6-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-fluoro-2-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-fluoro-2-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-fluoro-5-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-5-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-fluoro-2-(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-fluoro-2-(trifluoromethyl)benzoyl chloride ( 45.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,4-dichloro-5-fluorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4-dichloro-5-fluorobenzoyl chloride ( 45.48 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,5-diethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-diethoxybenzoyl chloride ( 45.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,5-diethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-diethoxybenzoyl chloride ( 45.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,5-dinitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-dinitrobenzoyl chloride ( 46.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,4,5-trimethoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4,5-trimethoxybenzoyl chloride ( 46.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl diphenylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of diphenylacetyl chloride ( 46.13 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-chloro-1-benzothiophene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloro-1-benzothiophene-2-carbonyl chloride ( 46.21 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (-)-menthoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (-)-menthoxyacetyl chloride ( 46.54 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl tridecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of tridecanoyl chloride ( 46.55 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-bromomethyl-benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-bromomethyl-benzoyl chloride ( 46.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (2-bromophenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2-bromophenyl)acetyl chloride ( 46.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 9-(methoxycarbonyl)nonanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 9-(methoxycarbonyl)nonanoyl chloride ( 46.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-heptylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-heptylbenzoyl chloride ( 47.75 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-[(trifluoromethyl)sulfanyl]benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-[(trifluoromethyl)sulfanyl]benzoyl chloride ( 48.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-(hexyloxy)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-(hexyloxy)benzoyl chloride ( 48.14 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 9-oxo-9H-fluorene-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 9-oxo-9H-fluorene-4-carbonyl chloride ( 48.53 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,4,6-trichlorobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,4,6-trichlorobenzoyl chloride ( 48.78 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl tetradecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of tetradecanoyl chloride ( 49.36 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-chloro-6-fluoro-1-benzothiophene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloro-6-fluoro-1-benzothiophene-2-carbonyl chloride ( 49.81 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-bromo-2-methoxybenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-bromo-2-methoxybenzoyl chloride ( 49.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride ( 50.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride ( 50.52 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarbonyl chloride ( 51.21 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-oxo-3H-benzo[f]chromene-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-oxo-3H-benzo[f]chromene-2-carbonyl chloride ( 51.73 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl pentafluorophenoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentafluorophenoxyacetyl chloride ( 52.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl pentadecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentadecanoyl chloride ( 52.16 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl pentachloropropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentachloropropionyl chloride ( 52.94 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl chloro(diphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of chloro(diphenyl)acetyl chloride ( 53.02 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-iodobenzoyl chloride ( 53.29 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 4-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-iodobenzoyl chloride ( 53.29 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride ( 54.81 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-(benzoyloxymethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-(benzoyloxymethyl)benzoyl chloride ( 54.93 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl hexadecanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of hexadecanoyl chloride ( 54.97 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,5-bis(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,5-bis(trifluoromethyl)benzoyl chloride ( 55.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2,5-bis(trifluoromethyl)benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2,5-bis(trifluoromethyl)benzoyl chloride ( 55.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 2-fluoro-5-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-fluoro-5-iodobenzoyl chloride ( 56.89 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride ( 58.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl (2-bromo-4,5-dimethoxyphenyl)acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of (2-bromo-4,5-dimethoxyphenyl)acetyl chloride ( 58.7 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3-benzyloxy-4-methoxy-2-nitrobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-benzyloxy-4-methoxy-2-nitrobenzoyl chloride ( 64.34 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 5-bromo-2-iodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-bromo-2-iodobenzoyl chloride ( 69.07 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 7-chloro-2-(4-chlorophenyl)-6-methyl-4-quinolinecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 7-chloro-2-(4-chlorophenyl)-6-methyl-4-quinolinecarbonyl chloride ( 70.12 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(2-methyl)phenyl 3,4,5-triiodobenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 2-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,4,5-triiodobenzoyl chloride ( 103.65 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl acetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of acetyl chloride ( 15.69 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of propanoyl chloride ( 18.5 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl cyclopropanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclopropanecarbonyl chloride ( 20.9 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl butanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of butanoyl chloride ( 21.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 2-methylpropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methylpropanoyl chloride ( 21.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl methoxyacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of methoxyacetyl chloride ( 21.7 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl chloroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of chloroacetyl chloride ( 22.58 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 4-pentenamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-pentenoyl chloride ( 23.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl cyclobutanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclobutanecarbonyl chloride ( 23.71 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl pentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of pentanoyl chloride ( 24.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 3-methylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methylbutanoyl chloride ( 24.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 3-chloropropanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-chloropropanoyl chloride ( 25.39 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl furan-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-furoyl chloride ( 26.1 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 5-isoxazolecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-isoxazolecarbonyl chloride ( 26.3 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl trifluoroacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of trifluoroacetyl chloride ( 26.49 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl cyclopentanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclopentanecarbonyl chloride ( 26.51 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl hexanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of hexanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 3,3-dimethylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3,3-dimethylbutanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 2-ethylbutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-ethylbutanoyl chloride ( 26.92 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl benzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of benzoyl chloride ( 28.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 4-chlorobutanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-chlorobutanoyl chloride ( 28.19 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 3-methylfuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methyl-2-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 2-methylfuran-3-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methyl-3-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 5-methylfuran-2-carboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-methyl-2-furoyl chloride ( 28.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 2-thiophenecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-thiophenecarbonyl chloride ( 29.31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl cyclohexanecarboxamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of cyclohexanecarbonyl chloride ( 29.32 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl heptanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of heptanoyl chloride ( 29.72 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 3-(methoxycarbonyl)propanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-(methoxycarbonyl)propanoyl chloride ( 30.11 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 4-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 4-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 2-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 2-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 3-methylbenzamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 3-methylbenzoyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl phenylacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of phenylacetyl chloride ( 30.91 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl 5-chloropentanamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of 5-chloropentanoyl chloride ( 31 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo. Purification via column chromatography affords the title compound.

(3-methyl)phenyl bromoacetamide

Pyridine (15.8g, 16.1 mL, 0.20 mol) is added to a stirred solution of 3-methyl-1-aminobenzene ( 21.43 g, 0.20 mol) in 500 mL of methylene chloride. The reaction mixture is stirred for ten minutes, and a solution of bromoacetyl chloride ( 31.47 g, 0.20 mol) in 500 mL of methylene chloride is added dropwise at room temperature. The reaction mixture is then stirred at room temperature for 18 hours. The resulting reaction mixture is then diluted with 400 mL of water and stirred vigorously. The aqueous layer is separated and washed three times with methylene chloride. The organic fractions are combined and dried via magnesium sulfate. The resulting solution is filtered and the filtrate is concentrated in vacuo.