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

HRID 39733

Reaction equation

HRID 39733 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-6ad15f2d3e544c06b2ee4d550dd2382c
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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