Sodium Carbonate → Methyl 2-(chloromethyl)pyridine-3-carboxylate

Participants

Reaction Steps

Methyl 2-methylpyridine-3-carboxylate 1-oxide (33.2 g, 199 mmol) was stirred in refluxing POCl3 (200 mL, 2146 mmol) for 3 hours. After cooling to room temperature, the reaction mixture poured into ice-water. The resulting dark solution was neutralized with solid sodium carbonate and the products extracted into ethyl acetate (3×). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography (silica, 2-20% ethyl acetate/hexanes) gave methyl 2-(chloromethyl)pyridine-3-carboxylate as an orange oil and methyl 6-chloro-2-methylnicotinate as a light yellow oil.

Provenance & Evidence