Hydrochloric Acid → 2,5-Diaminobenzonitrile

Participants

Reaction Steps

To a solution of 80 grams (0.356 mole) of stannous chloride dihydrate in 200 ml. of concentrated hydrochloric acid is added in portions over the course of about 5 minutes, 16.314 grams (0.1 mole) of 5-nitroanthranilonitrile. Water cooling is used and the internal temperature rises to about 50°. Stirring is continued for 4 hours and the mixture is allowed to stand overnight. The reaction mixture is cooled to 5° in an ice-bath and a cold 50% solution of sodium hydroxide added until the mixture is strongly basic. The mixture is extracted with methylene chloride. The methylene chloride extracts are washed with water and the solvent removed by distillation. There is obtained 11.51 grams (86.5%) of material melting at 85°-87°. Recrystallization from benzene-skellysolve B gives material melting at 86°-7°. The infrared spectrum is in agreement.

Provenance & Evidence