4-Amino-3-chlorobenzonitrile

873-74-5

21803-75-8

Step 1: N-chlorosuccinimide (12.4 g, 93 mmol) was slowly added to a stirred solution of 4-aminobenzonitrile (10.0 g, 84.7 mmol) in acetonitrile (100 mL) at 90 °C. After the addition was completed, the reaction mixture was stirred continuously at 90 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The concentrated residue was dissolved in 500 mL of dichloromethane and washed with 5% aqueous sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4-amino-3-chlorobenzonitrile as a brown solid (12.2 g, 95% yield).1H NMR (300 MHz, CDCl3) δ 7.54 (d, J = 1.7 Hz, 1H), 7.35 (dd, J = 1.8,8.4 Hz, 1H), 6.77 (d, J = 8.5 Hz, 1H ), 4.63 (br s, 2H).