Ammonium Chloride → (3-Amino-6-fluoro-2-phenylaminophenyl)acetonitrile

Participants

Reaction Steps

(6-Fluoro-3-nitro-2-phenylaminophenyl)acetonitrile (463 mg, 1.70 mmol), iron powder (194 mg, 3.41 mmol), and ammonium chloride (263 mg, 5.12 mmol) in methanol (10 mL) and water (3 mL) were heated at 90° C. for 1 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in water and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to yield the title compound as brown solid (228 mg, 55%). 1H NMR 400 MHz δ (CDCl3): 7.23-7.17 (2H, m), 6.95 (1H, t, J=8.9 Hz), 6.83 (1H, tt, J=7.4, 1.0 Hz), 6.77 (1H, dd, J=8.9, 5.5 Hz), 6.61-6.56 (2H, m), 5.12 (1H, br s), 3.79 (2H, br s), 3.59 (2H, d, J=1.2 Hz).

Provenance & Evidence