Hydrochloric Acid → 2-Amino-3-nitrobenzoic acid

Participants

Reaction Steps

A solution of 2-chloro-3-nitrobenzoic acid (5.00 g, 24.8 mmol), ammonium hydroxide (25.0 ml) and copper (1) chloride (50 mg) is heated hi a bomb at 125° for 20 hr and is then allowed to cool to 20°-25°. The solid residue is dissolved in water and the solution acidified with 3 N hydrochloric acid. The resultant mixture is filtered, washed, and dried to provide the 2-amino-3-nitrobenzoic acid, mp 201°-203; IR (mineral oil) 3478, 3345, 2954, 2925, 2855, 1692, 1677, 1571, 1559, 1520, 1512, 1442, 1271, 1259, 1130 cm-1 ; NMR (300 MHz, CDCl3 -MeOD) 8.38, 8.30, 6.66; MS (EI) m/e 182, 164.

Provenance & Evidence