2-Methoxybenzylamine → HCID 68541546, compound

Participants

Reaction Steps

To a solution of 2-oxoindoline-5-carboxylic acid (0.200 g, 1.12 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.477 g, 2.47 mmol), diisopropylethylamine (0.586 mL, 3.37 mmol) and catalytic amount of N,N-dimethylaminopyridine in N,N-dimethylformamide/acteonitrile (1:1, 4 mL) was added 2-methoxybenzylamine (0.295 mL, 2.26 mmol) and the reaction mixture stirred at room temperature for 1 h. The solvent was evaporated and the crude material was purified on a short silica gel column using dichloromethane containing 5% methanol as the eluent. This was followed by triturating from ethyl acetate to give 0.10 g (33% yield) of the yellow title compound: 1H NMR (DMSO-d6, 400 MHz) δ 10.60 (br s, 1H), 8.65 (t, J=6 Hz, 1H), 7.79-7.77 (m, 2H), 7.21 (t, J=8 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 6.98 (d, J=8 Hz, 1H), 6.90-6.84 (m, 2H), 4.42 (d, J=6 Hz, 2H), 3.81 (s, 3H), 3.53 (s, 2H); MS (ES) m/z 297 (M++1), m/z 295 (M−−1).

Provenance & Evidence