Phosphorus oxychloride → 4-Chloro-3-nitropyridine

Participants

Reaction Steps

To a suspension of 3-nitropyridin-4-ol (4.342 g, 31 mmol) in toluene (60 mL) was added POCl3 (11.6 mL, 124.4 mmol) at 0° C. The resulting mixture was warmed to room temperature, then heated to 110° C. for 14 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was poured into ice, and basified with saturated aqueous NH4Cl solution. The mixture was extracted with EtOAc (40 mL×2). The combined organic layers was washed with water, brine, dried (MgSO4) and concentrated to a brown oil, which solidified on standing. (3.68 g, 75% yield).

Provenance & Evidence