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

Temperature

40 °C

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.

1. stirringthe reaction mixture was stirred overnight at 40° C
2. temperatureAfter cooling to room temperature
3. customMost of the methanol was evaporated
4. extractionthe resulting mixture was extracted with 3×150 mL of CH2Cl2
5. washThe combined organic portions were washed with 250 mL of H2O and 150 mL of brine
6. dry with materialdried over Na2SO4
7. customAfter evaporation of the solvent
8. custom20.2 g of crude solid was obtained
9. distillationdistilled on a Kugelrohr at an oven temperature of 140° C.

ORD record

ord-a6e74fa9757f402e875e41557f882004

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586203B2