Acetic Anhydride → HCID 69431575, compound

Participants

Reaction Steps

Acetic anhydride (2.83 ml, 30.0 mmol), tetrabutylammonium bromide (161 mg, 0.500 mmol), potassium acetate (1.96 g, 20.0 mmol) and isoamyl nitrite (1.75 ml, 13.0 mmol) were added in that order to a solution of 4-(acetylamino)-2-fluoro-3-methylphenyl acetate (2.25 g, 9.99 mmol) in ethyl acetate (30 ml) at room temperature. The resulting mixture was slowly heated until heating under reflux was caused. Then, the mixture was stirred for 11 hours while maintaining the temperature. After cooling, the mixture was partitioned and extracted with water and ethyl acetate, and the organic phase was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 1-acetyl-4-fluoro-1H-indazol-5-yl acetate (1.00 g, 38%).

Provenance & Evidence