Methanol → Methyl 2-(3-aminophenyl)acetate hydrochloride

Participants

Reaction Steps

A suspension of 3-amino phenylacetic acid (5.0 g, 33 mmol) in methanol (50 ml) at 0° C. under argon was slowly treated with thionyl chloride (19.4 g, 165 mmol). After completion of addition, the reaction mixture was allowed to warm up to room temperature and stirred for 16 hours. The solvent was evaporated and the residue was triturated with ethyl ether to give 3-amino phenylacetic acid methylester hydrochloride (5.3 g, 96.8%) as a colorless solid. 1H NMR (CDCl3) δ 10.6 (s, 2 H), 7.42 (m, 4 H), 3.68 (s, 3 H). 3.66 (s,2 H); 13C NMR (CDCl3) 172.5, 137.3, 133.1, 131.2, 130.8, 125.9, 123.7, 53.5, 41.5.

Provenance & Evidence