In a 50 mL round-bottomed flask equipped with a magnetic stirrer, methyl 3-hydroxy-2-pyridinecarboxylate (3.5 g, 22.80 mmol), potassium carbonate (3.46 g, 25.0 mmol), iodomethane (4.87 g, 34.3 mmol), and N,N-dimethylformamide (20 mL) were added sequentially. The reaction mixture was stirred at room temperature for 18 h under nitrogen protection. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 mL) and water (10 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (3 × 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent being a hexane solution of 30% ethyl acetate to give 2.1 g of methyl 3-methoxypyridine-2-carboxylate in 54% yield.
