Water → 5-Iodo-1H-indazole

Participants

Reaction Steps

To a solution of 4-iodo-2-methylaniline (1.09 g, 4.68 mmol) in CH3CO2H (40 mL), were added NaNO2 (0.39 g, 5.65 mmol) and water (1 mL) at 10° C. The resulting mixture was stirred at room temperature for 6 hours. Upon completion, the reaction mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0˜40% EtOAc in petroleum ether) affording the title compound (0.90 g). 1H NMR (DMSO-d6, 400 MHz): δ 13.23 (br, 1H), 8.18 (s, 1H), 8.02 (s, 1H), 7.57 (d, 1H), 7.41 (d, 1H).

Provenance & Evidence