Hydrochloric Acid → 2-Amino-5-chlorobenzophenone

Participants

Reaction Steps

To a solution of p-chloroaniline (640 mg) in tetrachloroethane (5 ml), a solution of boron trichloride (640 mg) in tetrachloroethane (2.5 ml), benzonitrile (1 ml) and aluminum chloride (734 mg) are added under ice cooling, and the resultant mixture is refluxed for 6 hours. After cooling, the reaction mixture is mixed with 2 N hydrochloric acid (10 ml), heated at 70° to 80° C. for 20 minutes, and shaken with methylene chloride. The methylene chloride layer is evaporated to give a residue, to which 95% ethanol (5 ml) and 2 N sodium hydroxide (10 ml) are added. The mixture is refluxed for 1 hour to hydrolyze benzonitrile and shaken with methylene chloride. The methylene chloride layer is evaporated, and the residue is dissolved in benzene and chromatographed on a column of alumina, which is eluted with benzene. The benzene eluate affords 2-amino-5-chlorobenzophenone (486 mg), which is recrystallized from ether to give crystals melting at 99° C.

Provenance & Evidence