Hydrochloric Acid → 4-Chloro-2,6-dimethylpyridine

Participants

Reaction Steps

To a solution of concentrated HCl (10 ml) at 10° C. was added 2,6-dimethylpyridine N-oxide (3.0 g, 24.3 mmol) and the resulting white slurry was stirred at room temperature for 3 hours. The product was filtered and washed with iPrOH (2×10 ml) and dried at reduced pressure. The resulting solid was dissolved in POCl3 (10 ml) and heated at reflux for 8 hours then cooled to 0° C. The reaction was quenched carefully with saturated K2CO3 (40 ml) and extracted with dichloromethane (2×50 ml), dried (Na2SO4), filtered and concentrated at reduced pressure. The residue was dissolved in ethanol (20 ml) and NEt3 (5 ml) and heated at reflux for 24 hours then cooled to room temperature and concentrated at reduced pressure. Water (5 ml) was added to the residue the aqueous mixture was extracted with chloroform (2×10 ml). The organics were combined and washed with brine (10 ml), dried (Na2SO4), filtered and concentrated at reduced pressure to give the title compound as brown solid (1.0 g, 33%).

Provenance & Evidence