Methyl iodide → Ethyl 5-chloro-6-methoxypicolinate

Participants

Reaction Conditions

Reaction Steps

Silver carbonate (142.4 g) and methyl iodide (25 mL) were added to a solution of ethyl 5-chloro-6-hydroxypyridine-2-carboxylate (26.0 g) in chloroform (500 mL), and the mixture was stirred at 70° C. for seven hours. The reaction solution was filtered through celite, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) and purified again by silica gel column chromatography (hexane:ethyl acetate=20:1) to give ethyl 5-chloro-6-methoxypyridine-2-carboxylate as a white solid (22.3 g, 80%).

Provenance & Evidence