Methyl 3-amino-4-methylbenzoate → methyl 1H-indazole-6-carboxylate

Participants

Reaction Steps

To a solution of 3-amino-4-methylbenzoic acid methyl ester (25 g, 0.15 mol) in 1 L of acetic acid cooled to 0° C. was added a solution of NaNO2 (12.5 g, 0.182 mol) in 50 ml of water and the mixture was warmed to room temperature with stirring over 4 hours. The solution was concentrated in vacuo, the residue was triturated with water, the solid was filtered and washed with water and hexane to afford 19 g (71.6%) of methyl indazole-6carboxylate.

Provenance & Evidence