Acetic Anhydride → 1-Acetyl-4-bromo-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-2-methylaniline (2.00 mL, 16.0 mmol) and potassium acetate (1.60 g, 16.3 mmol) in toluene (160 mL) was added acetic anhydride (4.54 mL, 48.0 mmol) at room temperature, and the mixture was stirred at 60° C. for 30 min. Isoamyl nitrite (3.22 mL, 24.0 mmol) was added, and the mixture was stirred at 60° C. for 18 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a crudely purified product.

Provenance & Evidence