[Synthesis]
At room temperature, 4-chloro-3-cyanopyridine (20) (2.77 g, 20.0 mmol) was dissolved in methanol (5 ml) and 28% sodium methanol-methanol solution (5.0 g, 24.0 mmol) was slowly added. The reaction mixture was stirred for 1 hour and then concentrated under reduced pressure to remove the solvent. The residue was partitioned between ethyl acetate and ice brine. The organic layer was dried with anhydrous magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The resulting crude product was recrystallized with a small amount of isopropyl ether to give 3-cyano-4-methoxypyridine (2.3 g, 86% yield) as a white solid. The product was characterized by 1H-NMR (200 MHz, CDCl3): δ 4.02 (3H, s), 6.93 (1H, d, J = 5.8 Hz), 8.65 (1H, d, J = 5.8 Hz), 8.69 (1H, s). |