Acetic Anhydride → 1-Acetyl-5-iodo-6-methylindazole

Participants

Reaction Conditions

Reaction Steps

Acetic acid anhydride (6.9 mL, 72 mmol) was added to a slurry of 2,5-dimethyl-4-iodoaniline (6.0 g, 24 mmol) and potassium acetate (2.4 g, 24 mmol) in benzene (50 mL). The mixture was heated to 80° C. and isopentylnitrit (4.8 mL, 36 mmol) was added during 20 min. The mixture was stirred at 80° C. overnight, then cooled and filtered. The filtrate was evaporated and purified by column chromatography (SiO2, dichloromethane). Product containing fractions were pooled and concentrated. The subtitle compound (1.5 g, 21%) was obtained as crystals from ethyl acetate.

Provenance & Evidence