Methanol → Methyl 5-Amino-2-chlorobenzoate

Participants

Reaction Steps

To a solution of 5-amino-2-chlorobenzoic acid (6.0 g, 35 mmol) in anhydrous methanol (100 ml) was added dropwise thionyl chloride (15 ml) with stirring under a nitrogen atmosphere. After stirring for 3 hours the volatiles were removed by spin evaporation in vacuo and the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate and then water. The organic layer was concentrated by spin evaporation in vacuo with the addition of dichloromethane (3 times) to give methyl 5-amino-2-chlorobenzoate as a white solid (6.2 g, 95%). 1H-NMR (400 MHz, DMSO-d6): δ 7.20-7.14 (m, 1H), 7.13-7.02 (m, 1H), 6.73-6.67 (m. 1H), 3.89 (s, 3H). ES-LCMS m/z 186 (M+H).

Provenance & Evidence