Methanol → 2-Amino-3-chlorobenzoic acid

Participants

Reaction Steps

To a stirred solution of 3-chloro-2-nitrobenzoic acid (2.01 g, 10.0 mmol) in anhydrous methanol (100 mL) nickel(II)chloride hexahydrate (4.75 g, 20.0 mmol) was added, and the reaction mixture was cooled to room temperature. To this green solution was added NaBH4 (2.27 g, 60.0 mmol) in small portions over a period of 20 min. After the addition was complete, the reaction mixture was stirred at room temperature for 16 hours. The solvents were removed under vacuum and water (100 mL) was added, before neutralization to pH approximately equal to 4 with aqueous 2 N HCl. After extraction with methylene chloride (2×100 mL), the organic phase was separated, washed with water (100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. The solvent was removed under vacuum to give 2-amino-3-chlorobenzoic acid as an off-white solid. Yield 0.90 g (52%).

Provenance & Evidence