4-Chloro-7-(trifluoromethyl)quinoline → 4-Chloro-1-oxo-7-(trifluoromethyl)-1lambda~5~-quinoline

HRID 2193102Notes

Reaction equation

HRID 2193102 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:13])[F:14])=[CH:9][CH:10]=2)[N+:5]([O-:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 231281334-Chloro-1-oxo-7-(trifluoromethyl)-1lambda~5~-quinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 14 mL of a chloroform solution containing 0.90 g of 4-chloro-7-trifluoromethylquinoline, 1.04 g of m-chloroperbenzoic acid was added, and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was added with 15 mL of an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a yellow solid, 4-chloro-7-trifluoromethylquinoline N-oxide.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-062000aadd0d4ad186eb620fec498592
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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