Ammonium Chloride → 4-(4-Chlorophenoxy)pyridin-3-amine

Participants

Reaction Steps

To a refluxing mixture of iron powder (1.91 g, 34.43 mmol) and ammonium chloride (230 mg, 4.30 mmol) in ethanol (45 μL) and water (8 mL) was added 4-(4-chlorophenoxy)-3-nitropyridine (AMR01116, 1.57 g, 6.26 mmol) and the resulting mixture was stirred at reflux for 1 h. After removal of the solvent, the residue was diluted in aqueous sodium hydrogen carbonate (40 mL) and extracted with DCM (3×20 mL). The organic layer was dried (MgSO4), filtered and evaporated. Flashmaster chromatography of the crude product using DCM/MeOH 9:1 as eluent gave 4-(4-chlorophenoxy)-pyridin-3-ylamin (1.03 g, 75%) as a white solid, mp 104-106° C.

Provenance & Evidence