Ammonia → 2-Amino-3-chloro-6-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

Using two dropping funnels, a solution of 59 ml (0.78 mol) of a 25% strength solution of ammonia in 207 ml of water and a mixture of 135.2 g (0.64 mol) of 3-chloro-6-methylisatoic anhydride in 705 ml of DMF were added simultaneously over a period of 30 min with stirring at 85-90° C. to 150 ml of water, resulting in a strong evolution of gas. The mixture was stirred at 90° C. for 2 h and at 22° C. for 10 h. The reaction solution was concentrated under reduced pressure and the residue was triturated with methyl tert-butyl ether, filtered off with suction and dried. This gave 67.4 g (57% of theory) of the title compound as a yellowish powder of m.p. 124-128° C.

Provenance & Evidence