Water → 5-Acetyl-2-aminobenzonitrile

Participants

Reaction Steps

A stirred mixture of 35.5 g of 4'-amino-3'bromoacetophenone, 17.8 g of cuprous cyanide and 180 ml of dry dimethylformamide was heated at reflux, under nitrogen for 6 hours. After cooling, the mixture was treated with 180 ml of a solution of ferric chloride (prepared from 400 g of ferric chloride hexahydrate, 100 ml of concentrated hydrochloric acid and 600 ml of water) and stirred for 20 minutes at 60°-70° C. A 500 ml portion of water and 400 ml of dichloromethane were added. To facilitate phase separation, the mixture was filtered and then the filtrate was extracted with two 400 ml portions of dichlorometbane. The organic extracts were combined, washed with 200 ml of water and 200 ml of saturated sodium bicarbonate solution and the solvent removed in vacuo at 80° C. The residue was evaporated twice from 100 ml portions of toluene, giving a yellow solid, which was crystallized from ethanol, giving 14.35 g of the desired compound, mp 155°-159° C.

Provenance & Evidence