8-Methylquinoline → Quinoline, 8-methyl-, 1-oxide

HRID 2193105Notes

Reaction equation

HRID 2193105 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.ClC1C=CC=C(C(OO)=[O:20])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-:20])=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 119108-MethylquinolineHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium Bicarbonate

Product 1

HCID 12488418Quinoline, 8-methyl-, 1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 40 mL of a chloroform solution containing 2.0 g of 8-methylquinoline, 3.6 g of m-chloroperbenzoic acid was added, and the mixture was stirred at room temperature overnight. Thereto was added 1.0 g of m-chloroperbenzoic acid, and the mixture was stirred at room temperature overnight. An aqueous saturated sodium hydrogen carbonate solution was added to the reaction mixture, 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 2.2 g of a brown oily substance, 8-methylquinoline N-oxide.

Workup

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

Sources & evidence

ORD record
ord-790442ce48c6449fa8ea0feaad2edf65
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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