Acetic Anhydride → 4-Methyl-1H-indazole-5-carbonitrile

Participants

Reaction Steps

Acetic anhydride (2.1 ml, 22.3 mmol), tetra-n-butylammonium bromide (118 mg, 0.366 mmol), potassium acetate (1.44 g, 14.7 mmol) and isoamyl nitrite (1.3 ml, 9.68 mmol) were added to an ethyl acetate suspension (15 ml) of N-(4-cyano-2,3-dimethylphenyl)acetamide (1.38 g, 7.33 mmol) at room temperature, and then the reaction was carried out for 7 hours under reflux conditions. The reaction mixture was cooled, diluted with ethyl acetate, and then washed with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then distilled to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform) to obtain 4-methyl-1H-indazole-5-carbonitrile (1.24 g, 84.9%).

Provenance & Evidence