Methylamine → 3-hydroxy-N-methylbenzamide

Participants

Reaction Steps

A solution of 3-hydroxybenzoic acid methyl ester (2.00 g, 0.0131 mol), methylamine (0.06 mol) and methanol (30 mL) was heated to 155° C. for 12 hours in a sealed tube. The solvent was removed in vacuo and the product was purified by column chromatography over silica gel using a gradient elution from 5 to 8% methanol in dichloromethane to give 1.20 g (60.4%) of 3-hydroxy-N-methylbenzamide as a yellow solid. MS [M+H] 152.2, 1H NMR (CDCl3) δ (ppm) 7.55 (s, 1H), 7.30 (d, J=7.8 Hz, 1H), 7.18 (d, J=7.5 Hz, 1H), 7.01 (m, 1H), 6.65 (b, 1H), 6.20 (b, 1H), 3.03 (d, J=4.8 Hz, 3H).

Provenance & Evidence