Ammonia → Methyl 3-(aminomethyl)thiophene-2-carboxylate

Participants

Reaction Steps

To a solution of 3-(bromomethyl)thiophene-2-carboxylate (9.3 g, 39.6 mmol) in DMF (150 mL) was added 7.0 N NH3 in MeOH (150 mL). After stirring at room temperature for 1 h, the reaction was concentrated and purified by flash chromatography over silica gel (5%-10% MeOH/DCM) to provide methyl 3-(aminomethyl)thiophene-2-carboxylate (4.86 g, 72% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.83 (d, J=5.0 Hz, 1H), 7.28 (d, J=5.0 Hz, 1H), 4.45 (s, 2H), 3.94 (s, 3H); MS (EI) m/z=172.2 [M+1]+.

Provenance & Evidence