1,1'-Carbonyldiimidazole → N-Methoxy-N-methyl-1H-indazole-3-carboxamide

Participants

Reaction Steps

Indazole-3-carboxylic acid (15 g, 0.0925 mol) was dissolved in DMF (40 mL) at room temperature. Carbonyldiimidazole (17 g, 0.104 mol) was added. A solution of diisopropylethylamine (18 mL, 0.104 mol) and N,O-dimethylhydroxylamine HCl (10 g, 0.104 mol) in DMF (10 mL) was added in portions. The reaction was stirred at room temperature overnight. The reaction was taken up in ethyl acetate and washed repeatedly with 2-N HCl, water, and brine. The organic layer was evaporated to a yellow oil, and passed through a pad of silica gel with hexane/ethyl acetate (1:2). The resulting solid was washed with ethyl acetate to give the desired product as a white solid (11.40 g, 0.056 mol).

Provenance & Evidence