Ethyl 3-(4-nitrophenyl)-2-propenoate → Ethyl 3-(4-aminophenyl)propanoate

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Reaction Steps

A mixture of 3-(4-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. After filtration over Celite® and removal of the solvent, 14 g of 3-(4-aminophenyl)propionic acid ethyl ester was obtained. 1H NMR (400 MHz, CDCl3): δ 6.98 (d, J=8.0 Hz, 2H), 6.61 (d, J=8.4 Hz, 1H), 4.12 (q, J=7.2 Hz, 2H), 2.84 (t, J=8.0 Hz, 2H), 2.55 (t, J=7.6 Hz, 2H), 1.23 (t, J=7.2 Hz, 3H). MS (ESI): m/z: 194 (M+H+).

Provenance & Evidence