Ethyl-m-nitrocinnamate → Ethyl 3-(3-Aminophenyl)propionate

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Reaction Steps

A mixture of 3-(3-nitrophenyl)acrylic acid ethyl ester (16.5 g, 74.6 mmol) and Pd/C (1.65 g) in MeOH (200 mL) was stirred under 40 psi of H2 at RT for 2 h, then filtered through Celite®. After removal the solvent, 14 g of 3-(3-aminophenyl)propionic acid ethyl ester was obtained. 1H NMR (400 MHz, CDCl3): δ 7.11 (t, J=5.6 Hz, 1H), 6.67 (d, J=7.2 Hz, 1H), 6.63-6.61 (m, 2H), 4.13 (q, J=7.2 Hz, 2H), 2.87 (t, J=8.0 Hz, 2H), 2.59 (t, J=7.6 Hz, 2H), 1.34 (t, J=6.8 Hz, 3H); MS (ESI): m/z: 194 (M+H+).

Provenance & Evidence