Quinoline → Quinoline 1-oxide

HRID 565415

Reaction equation

HRID 565415 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(Cl)Cl>[N+:1]1([O-:19])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 15366Quinoline 1-oxideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round bottom flask containing a solution of quinoline (12.2 mmol) in 50 mL of DCM was added 5.3 g of m-CPBA (30.6 mmol). The reaction mixture was stirred for 24 h. The reaction mixture was then diluted DCM (100 mL), washed with 5% NaOH (2×100 mL), dried (MgSO4), filtered, and concentrated in vacuo to give solid quinoline-N-oxide (90-95% yield).

Workup

  1. washdiluted DCM (100 mL), washed with 5% NaOH (2×100 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29472094d7bb48d1b5d4d27df59d40c6
Source dataset
uspto-grants-2001_01
Patent number
US06172084B2

Linked notes

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