4-Aminobenzonitrile → 4-Amino-3-chlorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred, 60° C. solution of 4-cyanoaniline (20 g, 0.169 mol) in acetonitrile (200 mL) was added slowly N-chlorosuccinimide (24.8 g, 0.186 mol) to keep the reaction at reflux. After the addition of the N-chlorosuccinimide was complete, the reaction mixture was stirred at 60° C. for two hours. The solvent was then removed under reduced pressure. The residue was then dissolved in dichloromethane, washed with a 5% sodium hydroxide solution, dried (Na2SO4) and evaporated under reduced pressure to afford 24.5 g (95%) of the title compound, 2-chloro-4-cyanoaniline, as a tan solid; m.p. 93°-95° C.

Provenance & Evidence