Ethanol → 2-Amino-4-methoxy-biphenyl

Participants

Reaction Steps

A Parr bottle charged with 4-methoxy-2-nitrobiphenyl (27.6 g, 120 mmol), Raney nickel (1.5 g), ethanol (100 mL), and H2O (100 mL) was rocked under hydrogen (60 psi) for 3 h. The suspension was filtered through Celite, the cake washed with ethanol (500 mL) and tetrahydrofuran (500 mL), and the filtrate concentrated in vacuo. The residual suspension was digested with CH2Cl2 (300 mL), washed with H2O (300 mL), and the organic portion extracted with 1 N HCl (4×200 mL). The combined extracts were made basic with 50% NaOH, extracted with CH2Cl2 (3×200 mL), and the organic extracts washed with brine (300 mL), dried (K2CO3), filtered, and concentrated in vacuo to give 24 g (100%) of the title compound which was used without further purification: 1H NMR (300 MHz, CDCl3) δ 3.78 (s, 3H), 3.90 (br s, 2H), 6.34 (d, J=2 Hz, 1H), 6.41 (dd, J=8, 2 Hz, 1H), 7.03 (d, J=8 Hz, 1H), 7.15-7.33 (m, 2H), 7.36-7.41 (m, 3H).

Provenance & Evidence