2-Methyl-3-nitroaniline → 4-Nitroindazole

Participants

Reaction Steps

2-Methyl-3-nitroaniline (20 g) in acetic acid (˜200 mL) was treated with NaNO2 (20 g) in water (50 mL) at 4° C. (mechanical stirring). The reaction mixture was allowed to warm to room temperature and stir overnight. The solvent was removed under reduced pressure. The residue was treated with water (700 mL) and the mixture was filtered. The solid was dried at 45° C. in a vacuum oven overnight to provide the title compound. 1H NMR (DMSO-d6) δ 13.91 (s, 1H), 8.55 (s, 1H), 8.18 (d, 1H), 8.10 (d, 1H), 7.61 (dd, 1H); MS (ESI) m/z 164 (M+H)+.

Provenance & Evidence