Ammonium Chloride → 3-Amino-6-fluoro-2-phenylaminobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-fluoro-3-nitro-2-phenylaminobenzonitrile (2.7 g, 10.5 mmol) in a mixture of MeOH (50 mL) and water (20 mL) were added NH4Cl (3.23 g, 62.9 mmol) and iron powder (2.3 g, 41.9 mmol) and the reaction mixture was heated at 90° C. for 1 h. After cooling to RT, the solid was filtered through a pad of Celite® and the filtrate concentrated in vacuo. The resulting residue was partitioned between EtOAc and water and the aqueous phase was extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane) to afford the title compound (930 mg, 39%). LCMS (Method B): RT 3.27 min [M+H]+ 227.8.

Provenance & Evidence