Nitric Acid → HCID 15457055, compound

HRID 992871Notes

Reaction equation

HRID 992871 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)=[C:4]([F:20])[CH:3]=1.[N+:21]([O-])([OH:23])=[O:22]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:21]([O-:23])=[O:22])=[CH:6][C:5]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:16])([F:17])[F:15])=[CH:12][CH:13]=2)=[C:4]([F:20])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15457048HCID 15457048, compound

Product 1

HCID 15457055HCID 15457055, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1.0 g (3.3 mmol) of 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 10 ml of concentrated sulfuric acid, and 0.25 g (4.0 mmol) of fuming nitric acid was dropwise added thereto under cooling with ice, followed by stirring for 1 hour. This reaction solution was poured into ice water and extracted with ethyl acetate. After washing with water and a saturated sodium hydrogencarbonate aqueous solution, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and then, the obtained residue was purified by silica gel column chromatography to obtain 1.1 g (yield: 96%) of the desired product. Melting point: 139-140° C.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materiala saturated sodium hydrogencarbonate aqueous solution, the organic layer was dried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cc6562dd98a7486ea0a05fb401b26bf2
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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