Methanol → Benzoic acid, 3-amino-, methyl ester

Participants

Reaction Steps

Thionyl chloride (43 g, 361.34 mmol, 5.00 equiv) was added dropwise with stirring at 0° C. to a solution of 3-aminobenzoic acid (10 g, 72.92 mmol, 1.00 equiv) in methanol (100 mL) and allowed to react, with stifling, overnight under reflux. The resulting mixture was concentrated under vacuum and quenched by the addition of 50 mL of water/ice. The resulting solids were collected via vacuum filtration and dried in an oven under reduced pressure, affording 10.3 g (93%) of methyl 3-aminobenzoate as a white solid.

Provenance & Evidence