Nitric Acid → HCID 67915377, compound

HRID 1460308Notes

Reaction equation

HRID 1460308 reaction equation
[CH3:1][C:2]1[CH2:7][C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[N+:10]([O-:13])([OH:12])=[O:11]>O>[N+:10]([O-:13])([OH:12])=[O:11].[CH3:9][C:4]1[CH2:5][C:6](=[O:8])[CH:7]=[C:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67915373HCID 67915373, compound

Product 1

HCID 67915377HCID 67915377, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Dimethyl-4-pyridone (Chem. Abs., 84, 4811x, (1976)) (52.56 g, 0.427 mol) was dissolved in water (100 ml) at 50° C., and fuming nitric acid (40 ml) was added dropwise. The mixture was cooled in ice for 45 minutes, and then the pale buff crystals were filtered off, washed with a little water, and sucked dry to give 2,6-dimethyl-4-pyridone nitrate salt, (46.79 g, 59%). This material was added in portions to a mixture of fuming sulphuric acid (23 ml) and fuming nitric acid (31 ml) at room temperature, and the mixture was heated to 100° C. and held there for 51/2 hours. The mixture was poured onto ice and neutralised with saturated aqueous potassium carbonate. The pale yellow solid which precipitated was filtered off and placed in a Soxhlet extractor and extracted with boiling isopropanol. The isopropanol was removed under reduced pressure to give the title compound, (26.5 g, 63%).

Workup

  1. temperatureThe mixture was cooled in ice for 45 minutes
  2. filtrationthe pale buff crystals were filtered off
  3. washwashed with a little water
  4. customsucked dry

Sources & evidence

ORD record
ord-2a1389f5bf5f4da7ba17909a0e4dfbd4
Source dataset
uspto-grants-1991_12
Patent number
US05070205

Reaction notes

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