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

HRID 133099

Reaction equation

HRID 133099 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2>ClCCl>[CH3:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N+:21]([O-:9])=[CH:20][CH:19]=[CH:18]2

Participants

4

Reactant 2

HCID 119108-MethylquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.45 g of m-chloroperbenzoic acid in 15 ml of dichloromethane is added dropwise to a solution of 1 g of commercially available 8-methylquinoline in 15 ml of dichloromethane. The reaction mixture is stirred over night diluted with 30 ml of dichloremethane and extracted two times each with 50 ml of halfsaturated aqueous sodium hydrogencarbonate solution. The organic layer is dried over magnesium sulfate, filtered and evaporated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 98:2). 1 g of the title compound are obtained as colourless solid.

Workup

  1. additiondiluted with 30 ml of dichloremethane
  2. extractionextracted two times each with 50 ml of halfsaturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue is chromatographed on silica gel (dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-ad3c59b8ebdc4483b2bd12794794eebd
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Linked notes

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