Acetic Acid → methyl 1H-indazole-6-carboxylate

Participants

Reaction Steps

2.47 g (34.5 mmol) of sodium nitrite was dissolved in 3.8 ml of water, and it was added dropwise to a mixture of 5.64 g (34.1 mmol) of methyl 3-amino-4-methyl-benzoate and 140 ml of acetic acid under ice-cooling. After the temperature of the reaction mixture was allowed to warm to room temperature and the mixture was stirred overnight, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over magnesium sulfate and filtered. The solvent was distilled off to give 4.83 g (yield: 80%) of methyl indazole-6-carboxylate.

Provenance & Evidence