Ammonia → 4-Nitroindazole

Participants

Reaction Steps

A solution of 2-methyl-3-nitro-aniline (5.00 g, 32.9 mmol) in glacial acetic acid (750 mL) was treated with a solution of sodium nitrite (2.27 g, 32.9 mmol) in water (7.5 mL). The resultant solution was stirred for 15 minutes and allowed to stand at room temperature for 3 days. The acetic acid was removed in vacuo, leaving a pale yellow solid which was dissolved in ethyl acetate (250 mL) and filtered through a plug of silica gel, rinsing with ethyl acetate. The ethyl acetate was removed in vacuo to afford a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.65 (dd, 1H, J1=7.46, J2=8.48), 8.10 (d, 1H, J=8.48), 8.16 (d, 1H, J=7.46), 8.54 (s, 1H), 13.93 (s, 1H); MS (DCI/NH3) m/z 164 [M+H]+.

Provenance & Evidence