Nitric Acid → 4-hydroxy-6-isopropyl-3-nitro-1H-pyridin-2-one

HRID 895547Notes

Reaction equation

HRID 895547 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

Reactant 2

HCID 944Nitric AcidHCID 546965906-Isopropylpyridine-2,4-diol

Product 1

HCID 546965894-hydroxy-6-isopropyl-3-nitro-1H-pyridin-2-one

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

  1. temperatureAfter cooling
  2. customThe solid that precipitates
  3. filtrationis collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-93372147b8ea4bc6a683e5d097fe3def
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

Loading…