Nitric Acid → 4-hydroxy-6-isopropyl-3-nitro-1H-pyridin-2-one
Reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[NH:5][C:4](=[O:11])[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>>[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[NH:5][C:4](=[O:11])[C:3]=1[N+:12]([O-:14])=[O:13]Participants
3
Procedure
A solution of 4-hydroxy-6-isopropyl-1H-pyridin-2-one (1.76 g, 11.5 mmol) in 55-60 mL of 50% aq HNO3 is stirred at 70° C. for 2.5 h. After cooling, the reaction mixture is poured into ice-cold H2O (˜100 mL). The resulting solution is allowed to sit in the refrigerator for 3.5 days. The solid that precipitates is collected by filtration, washed with water, and dried to afford 4-hydroxy-6-isopropyl-3-nitro-1H-pyridin-2-one as yellow crystals. 1H NMR (DMSO-d6, 300 MHz) δ 12.30 (br s, 1H), 11.82 (br s, 1H), 5.82 (d, J=1.2 Hz, 1H), 2.71 (sept, J=6.9 Hz, 1H), 1.13 (d, J=6.9 Hz, 6H) ppm.
Workup
- temperatureAfter cooling
- customThe solid that precipitates
- filtrationis collected by filtration