Ethyl 4-nitrocinnamate → Ethyl 3-(4-aminophenyl)propanoate

Participants

Reaction Steps

A mixture of (E)-ethyl 3-(4-nitrophenyl)acrylate (commercially available from Aldrich, 5.00 g, 26.0 mmol) and 2.8 g of 10% Pd/C (wet, 50% water) in MeOH (26 mL) was shaken under 20 psi of hydrogen at room temperature for 20 hours. The mixture was then filtered through a pad of celite, the filtrate was concentrated, and the residue was purified through a short column of silica gel using 20% EtOAc/hexane as the eluent to give 3.48 g (69%) of the desired product ethyl 3-(4-aminophenyl)propanoate 47.2. MS ESI (pos.) m/e: 194 (M+H)+.

Provenance & Evidence