Dimethyl Sulfate → Methyl 2,6-dichloropyridine-3-carboxylate

Participants

Reaction Steps

To the mixture of 2,6-dichloro-nicotinic acid (4.7 g, 22 mmol) and acetone (22 ml), potassium carbonate (4.6 g, 33 mmol) and dimethylsulfate (2.4 ml, 24 mmol) were sequentially added at room temperature, and the obtained reaction mixture was stirred at room temperature for 16 hours. Impurities were removed by filtration, and the solvents were evaporated under reduced pressure from the filtrate. Dichloromethane was added to the obtained residue, followed by washing with a saturated sodium bicarbonate aqueous solution. The obtained organic layer was dried using anhydrous sodium sulfate, and the solvents were evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=10:1 to 1:1), thereby obtaining the entitled compound (4.0 g, 87%).

Provenance & Evidence