Ammonium Chloride → 4-[(6-Methylpyridin-3-yl)oxy]pyridin-3-amine

Participants

Reaction Steps

To a refluxing mixture of iron powder (2.55 g, 45.93 mmol) and ammonium chloride (307 mg, 5.74 mmol) in ethanol (45 mL) and water (8 mL) was added 4-(6-methyl-pyridin-3-yloxy)-3-nitropyridine (AMR01121, 1.93 g, 8.35 mmol) and the resulting mixture was stirred at reflux for 2 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. Flash master chromatography of the crude product using DCM to DCM/MeOH 9:1 gradient as eluent gave 4-(6-methylpyridin-3-yloxy)-pyridin-3-ylamine (1.32 g, 79%) as an orange solid, mp 74-79° C.

Provenance & Evidence