Hydrochloric Acid → N-(pyridin-2-yl)formamide

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium methoxide (176 mL, 25 wt %, 0.81 mol) in 500 mL of methanol was added 2-aminopyridine (30.0 g, 0.32 mol) and the resulting solution was stirred at 40° C. for 30 minutes. Ethyl formate (220 mL, 2.76 mol) was then added dropwise and the reaction mixture was stirred overnight at 40° C. After cooling to room temperature, 250 mL of H2O and 250 mL of CH2Cl2 were added and conc. HCl (˜40 mL) was added dropwise until pH ˜5. Most of the methanol was evaporated and the resulting mixture was extracted with 3×150 mL of CH2Cl2. The combined organic portions were washed with 250 mL of H2O and 150 mL of brine and dried over Na2SO4. After evaporation of the solvent, 20.2 g of crude solid was obtained and distilled on a Kugelrohr at an oven temperature of 140° C. to yield 18.98 g of a white solid as the product.

Provenance & Evidence