Nitric Acid → HCID 22277469, compound

Participants

Reaction Conditions

Reaction Steps

5-Cyclopentyl-1H-pyrazol-3-carboxylic acid (13 g, 72.1 mmol) was added portionwise to concentrated sulfuric acid (75 ml) at room temperature with stirring. The reaction mixture was then heated to 60° C. and concentrated nitric acid (70%, 12.7 ml, 202 mmol) was added dropwise, keeping the temperature at 60° C. The reaction was then stirred at 60° C. for 3 hours, cooled to room temperature and poured onto 50 ml of ice with stirring. After 15 minutes the precipitate was isolated by filtration, washed with water and dried under reduced pressure to give 5-cyclopentyl-4-nitro-1H-pyrazol-3-carboxylic acid (7.1 g) as a yellow solid. 1H NMR (400 MHz, DMSO-D6): δ=14.00-14.41 (1H, brs), 13.28-13.85 (1H, brs), 3.20-3.56 (1H, brs, partially masked by solvent), 1.96-2.10 (2H, m), 1.54-1.80 (6H, 2×m) ppm. LRMS (electrospray): m/z [M−H]+ 224, [2M−H]+ 449. Anal. Found C, 43.83; H, 5.35; N, 16.94. C9H11N3O4. 1.2 mol H2O requires C, 43.80; H, 5.47; N, 17.02%.

Provenance & Evidence