Acetic Anhydride → HCID 59834364, compound

Participants

Reaction Steps

A mixture of N-[2-(2,4-difluorophenoxy)-5-methylpyridin-4-yl]acetamide (2.3 g), acetic anhydride (2.6 g), acetic acid (2.7 mL) and potassium acetate (1.7 g) in 40 mL of benzene was brought to reflux. A solution of isoamyl nitrite (1.5 mL) in 10 mL of benzene was added to the refluxing solution over a period of two hours and refluxing was continued for an additional 18 hours. The reaction mixture was cooled and stirred with 50 mL of a 5% aqueous sodium carbonate solution for 3 hours. The organic layer was separated, dried, concentrated and purified via chromatography (silica gel, 8% ethyl acetate/hexane) to give 0.27 g of 1-[6-(2,4-difluorophenoxy)pyrazolo[4,3-c]pyridine-1-yl]ethanone (11% yield). Mass Spec. M+H=290.

Provenance & Evidence