A solution was prepared by dissolving 2-chloro-4-methyl-3-nitropyridine (250 g, 1.45 mol) in methanol (1.0 L). This solution was slowly added dropwise (taking 2 hours) to a stirring solution of sodium methanolate (250 μL, 4.63 mol) in methanol (850 mL) at 0 °C. After the dropwise addition, the reaction mixture was heated to reflux and maintained for 23 h, during which time the progress of the reaction was monitored by thin-layer chromatography (TLC) to confirm the completion of the reaction. Upon completion of the reaction, the mixture was concentrated to about 900 mL under reduced pressure, followed by the addition of water (1.5 L) to quench the reaction. The precipitated solid product was collected by filtration, washed with water and dried under reduced pressure to afford 2-methoxy-3-nitro-4-methylpyridine (250 g, 100% yield) as a brown solid. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.22 (d, J = 5.2 Hz, 1H), 7.10 (d, J = 5.6 Hz, 1H), 3.92 (s, 3H), 2.26 (s, 3H).
