(RS)-ethyl 2-(4-nitrophenyl)-heptanoate → (RS)-ethyl 2-(4-aminophenyl)-heptanoate

Participants

Reaction Steps

12 g of (RS)-ethyl 2-(4-nitrophenyl)-heptanoate dissolved in 100 ml of ethanol was treated with 2.4 g of 10% palladium on carbon. The mixture was stirred at room temperature for 18 hours under 40 psi of hydrogen. The mixture was filtered on a pad of Celite and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 25% ethyl acetate/hexanes), yielding 10.4 g of a pale yellow oil. 1H NMR (CDCl3): 7.10 (d, J=8.4 Hz, 2H), 6.63 (d, J=8.5 Hz, 2H), 4.20-4.00 (m, 2H), 3.61 (br. s, 2H), 3.40 (t, J=7.7 Hz, 1H), 2.05-1.90 (m, 1H), 1.75-1.60 (m, 1H), 1.30-1.15 (m, 6H), 1.20 (t, J=7.2 Hz, 3H), 0.85 (t, J=6.7 Hz, 3H).

Provenance & Evidence