4-Iodo-o-toluidine → 5-Iodo-1H-indazole

Participants

Reaction Steps

A solution of 4-iodo-2-methylaniline (10.0 g, 42.9 mmol) in glacial acetic acid (400 mL) was treated with a solution of NaNO2 (2.96 g, 42.9 mmol) in water (10 mL). After stirring for 6 hours, the mixture was concentrated to dryness and dissolved in ethyl acetate (EtOAc). Filtration through a pad of silica gel (EtOAc) provided the title compound (10.4 g, 99%) as a deep purple solid: ESI MS m/z 245 [M+H]+.

Provenance & Evidence