Methanol → 4-Fluoro-N2-pyridin-4-yl-benzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of (5-fluoro-2-nitro-phenyl)-pyridin-4-yl-amine (375 mg, 1.61 mmol) in a 3:1 mixture of MeOH:water (40 mL) were added NH4Cl (516 mg, 9.65 mmol) and iron powder (359 mg, 6.43 mmol) and the reaction mixture heated at 80° C. for 2 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 a saturated aqueous solution of NaHCO3. The organic fraction was dried and concentrated in vacuo to afford the title compound as a dark beige solid (215 mg, 66%). LCMS (Method C): RT 1.32 min [M+H]+ 204.09

Provenance & Evidence