Sodium Hydroxide → 4-(Aminomethyl)-2-chloroaniline

Participants

Reaction Steps

To lithium aluminum hydride (2.11 g, 55.6 mmol) in dry THF (50 mL) was added dropwise 4-amino-3-chlorobenzonitrile (3.29 g, 21.6 mmol) in THF (40 mL). The mixture was stirred at RT for 16 hours. Then, 6.0 mL of 1.0 N NaOH solution was added dropwise and the reaction mixture was stirred for 20 min. The solid was filtered off and washed with THF for three times. The solvent was removed by rotavap to give 4-amino-3-chlorobenzylamine as an oily liquid (3.04 g, 90%). 1H NMR (500 MHz, CD3OD): δ 7.18 (d, J=2Hz, 1H), 7.00 (dd, J=8Hz, 2Hz, 1H), 6.78 (d, J=8Hz, 1H), 3.61 (s, 2H).

Provenance & Evidence