Nitric Acid → HCID 18408320, compound

HRID 992893Notes

Reaction equation

HRID 992893 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:12][C:13]=2[Cl:14])=[CH:4][CH:3]=1.[N+:21]([O-])([OH:23])=[O:22]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]([C:15]([F:16])([F:17])[F:18])=[CH:12][C:13]=2[Cl:14])=[CH:6][C:7]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 18408343HCID 18408343, compound

Product 1

HCID 18408320HCID 18408320, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

0.2 g (0.62 mmol) of 3-(4-chlorophenyl)-4-chloro-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 2 ml of concentrated sulfuric acid, and 0.04 g (0.64 mmol) of fuming nitric acid was added thereto under cooling with ice, followed by stirring for 1 hour. After completion of the reaction, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium hydrogencarbonate aqueous solution and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained crude crystals were washed with isopropyl ether to obtain 0.21 g (yield: 91%) of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium hydrogencarbonate aqueous solution and dried over anhydrous magnesium sulfate
  6. distillationThe organic layer was distilled off under reduced pressure
  7. customthe obtained crude crystals
  8. washwere washed with isopropyl ether

Sources & evidence

ORD record
ord-20f040aec672430fa21317a6e8cf0b2b
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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