Acetic Anhydride → 1-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

Participants

Reaction Steps

Acetic anhydride (4.73 ml) was added to the mixture of 4-bromo-2-ethylaniline (5.0 g) and KOAc (2.94 g) in CHCl3 (70 ml) and stirred for 30 min at reflux. Then isoamyl nitrite (6.65 ml) and 18-crown-6-ether (660 mg) was added to the reaction mixture and stirred for 12 h at reflux. The reaction mixture was diluted with CHCl3, washed with water, and dried over sodium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography (hexane/ethyl acetate), and crystallized from mixed solvent of hexane and CHCl3 to give the title compound as a yellow solid.

Provenance & Evidence