Methanol → Methyl 2,6-dichloropyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 2,6-dichloronicotinic acid (20.2 g, 0.105 mol) in MeOH (500 mL) was cooled to 0 ° C. and neat thionyl chloride (38 mL, 63 g, 0.525 mol) was added over ˜0.5 hours. The reaction mixture was stirred at 0° C. for 1 hour. The cooling bath was removed, the reaction temperature was allowed to warm to 25° C., and the reaction was allowed to stir for an additional 2 days at 25° C. The solvent was removed under reduced pressure to give an off-white residue. The residue was dissolved in Et2O (˜500 mL) and the resulting solution was washed successively with saturated aqueous NaHCO3 solution (˜300 mL), water (˜300 mL), and brine solution (˜300 mL). The organic layer was separated, dried over anhydrous MgSO4, and filtered. Removal of the solvent under reduced pressure yielded methyl 2,6-dichloronicotinate (21.0 g, 97%) as a white solid.

Provenance & Evidence