m-Chloroperbenzoic acid → 4-Methoxyquinoline 1-oxide

HRID 39729

Reaction equation

HRID 39729 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:21])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N+:6]([O-:21])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 5219384-Methoxyquinoline

Product 1

HCID 108559994-Methoxyquinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 25 mL of a chloroform solution containing 1.72 g of 4-methoxyquinoline, 3.16 g of m-chloroperbenzoic acid was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was added with 20 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 light brown oily substance, 4-methoxyquinoline 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-a15e95c74e084d5782cf41f7f43d5ff4
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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