Methanol → 3-Amino-2-methylbenzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To 3-amino-2-methylbenzoic acid (500 mg, 3.3 mmol) in methanol (20 ml) was added sulfuric acid (500 μl) and heated to 70° C. for 22 h, at which point the volume was reduced by rotary evaporation. The residue was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The resultant organic layer was dried over sodium sulfate, filtered, and then concentrated to afford a tan oil (125 mg, 23%) of methyl 3-amino-2-methylbenzoate, which was used without further purification. 1H NMR (400 MHz, DMSO-d6): 6.99-6.93 (m, 1H), 6.89-6.86 (d, 1H), 6.81-6.78 (d, 1H), 5.12-5.07 (br. s, 2H), 3.78 (s, 3H), 2.16 (s, 3H). MS (EI) for C9H11NO2: 166 (MH+).

Provenance & Evidence