Ammonium Chloride → 3-Amino-4-(2-cyano-ethylamino)-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of ammonium chloride (21.7 g, 406.3 mmol) in water (200 mL) was added 4-(2-cyanoethylamino)-3-nitro-benzoic acid methyl ester (6.1 g, 24.5 mmol) followed by zinc powder (42.8 g, 655.9 mmol). The mixture was heated to 60° C. for 3 h. It was filtered hot and washed with EtOAc. The filtrate was further extracted with EtOAc and the combined organic phase washed with brine solution. The organic layer was evaporated to give 4.1 g (75%) of 3-amino-4-(2-cyano-ethylamino)-benzoic acid methyl ester. MS-ESI m/z 220 (M+1); 1H NMR (300 MHz, CDCl3) δ 2.7 (t, 2H), 3.6 (m, 2H), 3.8 (s, 3H), 4.3 (bs, 1H), 6.6 (d, 1H), 7.45 (d, 1H), 7.6 (d, 1H)

Provenance & Evidence