Hydrochloric Acid → Ethyl 4-(4'-amino-3-methyl-1,1'-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate

Participants

Reaction Steps

A mixture of ethyl 4-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (3.40 g, 7.60 mmol), iron powder (4.20 g, 76.00 mmol), 2 N aqueous hydrochloric acid (3.80 mL, 7.60 mmol), and 85/15 ethanol/water (100 mL) was stirred at reflux for 2.5 h. The reaction mixture was filtered through a pad of Celite®, and concentrated to give ethyl 4-(4′-amino-3-methyl-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate as a light, brown solid (2.94 g, 93% yield). LC-MS ret. time 3.23 min, m/z 416.1 (MH+); 1H NMR (CDCl3) δ 1.32 (t, 3H), 1.82–2.17 (m, 2H), 2.58 (s, 3H), 2.68–2.77 (m, 2H), 2.98–3.09 (m, 2H), 3.49 (dd, 1H), 3.74 (br s, 2H), 4.10 (q, 2H), 6.79 (d, 2H), 7.12–7.37 (m, 5H), 7.38–7.54 (m, 4H), 7.78 (d, 1H).

Provenance & Evidence