Sulfuric Acid → 2,3-Dimethyl-6-nitro-2H-indazole

Participants

Reaction Conditions

Reaction Steps

3-methyl-6-nitro-2H-indazole (0.85 g, 5 mmol, 1 equiv) was dissolved in DMSO (4 ml) and treated with sulphuric acid (0.26 ml, 5 mmol, 1 equiv) to yield a thick slurry that was treated with dimethylsulfate (1.36 ml, 14 mmol, 2.8 equiv). The reaction mixture was heated to 50° C. under nitrogen for 72 hrs. The reaction mixture was cooled down to room temperature and treated with a saturated solution of sodium bicarbonate (10 ml). The reaction mixture was extracted with DCM (2×20 ml). The organic layers were washed with water (20 ml). Propanol was added and the organic layers were evaporated under vacuum to yield a solid which was filtered and washed with heptane (5 ml). The desired compound was collected as a brown solid (0.48 g, 50%).

Provenance & Evidence