Nitric Acid → HCID 19877189, compound

HRID 1088665Notes

Reaction equation

HRID 1088665 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1.[N+:10]([O-:13])([OH:12])=[O:11]>O>[N+:10]([O-:13])([OH:12])=[O:11].[CH3:1][C:2]1[NH:3][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 836092,6-Dimethylpyridin-4(1H)-one

Product 1

HCID 19877189HCID 19877189, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Dimethyl-4(1H)-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, the pale buff crystals obtained were filtered off, washed with a little water, and sucked dry to give 2,6-dimethyl-4(1H)-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 at this temperature for 5.5 hours. The mixture was poured onto ice and neutralised with saturated aqueous potassium carbonate. The pale yellow solid which precipitated was filtered off and extracted with boiling isopropanol in a Soxhlet extractor. 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. customthe pale buff crystals obtained
  3. filtrationwere filtered off
  4. washwashed with a little water
  5. customsucked dry

Sources & evidence

ORD record
ord-13c544e3d08b4c8296c4fbf550af8a27
Source dataset
uspto-grants-1990_10
Patent number
US04963560

Reaction notes

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