Acetic Acid → HCID 21936423, compound

Participants

Reaction Steps

To an ice-bath cooled solution of sodium borohydride (5.47 g, 144.5 mmol) in anhydrous 1,4-dioxane (100 ml) was added slowly a solution of glacial acetic acid (8.27 ml, 144.5 mmol) in 1,4-dioxane (50 ml). To this mixture was added 6-(4-fluorophenyl)nicotinamide (Description 24; 6.25 g, 28.9 mmol) and the resulting mixture heated at reflux for 4 hours. The cooled reaction mixture was evaporated and water (60 ml) added slowly. This mixture was extracted with dichloromethane, and the solid which appeared between the layers was removed by filtration. This solid was triturated with a mixture of dichloromethane and iso-hexanes, filtered and dried to give the title compound (510 mg, 8%) as a pale green solid.

Provenance & Evidence