(3-Fluoro-2-methoxy-6-nitrophenyl)phenylamine → 4-Fluoro-3-methoxy-N2-phenylbenzene-1,2-diamine

Participants

Reaction Steps

To a solution of (3-fluoro-2-methoxy-6-nitrophenyl)phenylamine (322 mg, 1.2 mmol) in EtOAc (5 mL) was added palladium on carbon (30 mg, 10% by wt) and the reaction mixture stirred at RT under an atmosphere of hydrogen for 4 hours. The reaction mixture was filtered and the filtrate concentrated in vacuo to give the title compound as a white solid which darkened to red on standing (284 mg, 100%). 1H NMR 400 MHz δ (CDCl3): 7.24-7.18 (2H, m), 6.88-6.78 (2H, m), 6.71-6.66 (2H, m), 6.43 (1H, dd, J=9.0, 4.5 Hz), 5.50 (1H, br s), 3.77 (3H, d, J=1.7 Hz), 3.64 (2H, br s).

Provenance & Evidence