Sulfuric Acid → HCID 86680019, compound

Participants

Reaction Steps

4-Methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-ol (610 mg, 2.40 mmol) was dissolved in acetonitrile (4 mL) and cooled to 0° C. before concentrated sulphuric acid (2.1 mL) was added dropwise. The reaction was allowed to warm to room temperature and stirred for 1 hr before being poured onto ice (150 g), basified with KOH and extracted with DCM (2×30 mL). The combined organic layers were washed with brine (20 mL), passed through a phase separation cartridge and concentrated under reduced pressure to give N-(4-methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide as a yellow solid (660 mg, 93%). 1H NMR (400 MHz, CDCl3) δ 8.05-7.98 (m, 1H), 5.31 (s, 1H), 3.81-3.73 (m, 3H), 3.35 (ddd, J=14.2, 9.3, 2.2 Hz, 1H), 3.22 (t, J=5.9 Hz, 2H), 3.09 (ddd, J=14.2, 7.6, 2.5 Hz, 1H), 2.43-2.31 (m, 2H), 2.05-1.95 (m, 3H), 1.89-1.74 (m, 4H), 1.53-1.36 (m, 3H).

Provenance & Evidence