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

HRID 1626424Notes

Reaction equation

HRID 1626424 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=C(C=CC=1)C(OO)=[O:17]>C(Cl)Cl.CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-:17])=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 119108-MethylquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 12488418Quinoline, 8-methyl-, 1-oxideYield 39.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-methylquinoline (1.00 g, 6.98 mmol) in DCM (21 ml) was added 3-chlorobenzoperoxoic acid (2.35 g, 10.5 mmol), and the reaction was stirred for 16 hours at ambient temperature. The reaction was diluted with EtOAc and washed with 20% sodium sulfite, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified on the silica gel eluting with a gradient of 1-10% MeOH/DCM to yield the desired compound (0.440 g, 2.76 mmol, 39.6% yield).

Workup

  1. washwashed with 20% sodium sulfite, saturated sodium bicarbonate, and saturated sodium chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on the silica gel eluting with a gradient of 1-10% MeOH/DCM

Sources & evidence

ORD record
ord-2348c1c0e36641ce80b6b31386436e5b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…