5-Chloro-2-methylaniline → N-(5-Chloro-2-methylphenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-methyl-phenylamine (50 g, 353.11 mmol) was dissolved in dry THF (500 mL) followed by addition of triethylamine (61.53 mL, 441.39 mmol) and the whole heated to 60° C. To the stirring solution at 60° C. was added dropwise a solution of acetic anhydride (50 ml, 529.66 mmol) in dry THF (100 mL) and the reaction was stirred at 60° C. overnight. Upon cooling, the reaction was diluted with H2O (500 mL), ethyl acetate (250 mL) and the layers separated. The organics were washed with H2O (250 mL), 1N HCl (250 mL), sat Na2CO3 (250 mL), brine (250 mL), dried (MgSO4) and concentrated to a solid (59.67 g, 324.97 mmol).

Provenance & Evidence