Methanol → HCID 22596370, compound

Participants

Reaction Steps

To a mixture of 3-(2-nitrophenylamino)benzonitrile (2.0 g, 8.40 mmol) in a 3:1 mixture MeOH:water (120 mL) were added NH4Cl (2.70 g, 0.05 mol) and iron powder (1.88 g, 0.03 mol) and the reaction mixture heated at reflux temperature for 1 h. After cooling to RT, the solid was filtered through a pad of Celite® and washed with additional MeOH. The filtrate was concentrated in vacuo and the resulting residue partitioned between DCM and water. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% MeOH in DCM) to afford the title compound as a yellow solid (185 mg, 11%). LCMS (Method J): RT 2.99 min [M+H]+ 210.0.

Provenance & Evidence