Sodium hydride → N-formyl-N-(pyridin-2-yl)formamide

Participants

Reaction Steps

To a suspension of sodium hydride (10.8 g, 60 wt %, 0.27 mol) in 50 mL of THF was added dropwise a solution of N-(pyridine-2-yl)formamide (22.4 g, 0.18 mol) in 250 mL of THF. When the addition was complete, the reaction was stirred at room temperature for 30 minutes and then cooled in an ice/salt bath. The acetic formic anhydride ethereal solution from the previous step was added in one portion. The resulting mixture was stirred in the ice bath for 30 minutes and then overnight at room temperature. The mixture was poured into 1 L of ice/water and extracted with 3×250 mL of CH2Cl2. The combined organic extracts were washed with 2×250 mL of H2O, dried and evaporated to give 33.2 g of solid. The crude product was column chromatographed (silica gel) eluting with 100% CH2Cl2 followed by 90:10 CH2Cl2:EtOAc. 14.2 g of product was isolated as a white solid.

Provenance & Evidence