7-Methylquinoline → 7-Methylquinoline 1-oxide

HRID 922746Notes

Reaction equation

HRID 922746 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:17]>C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 119277-MethylquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 232711687-Methylquinoline 1-oxideYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Methylquinoline (1-1, 240 g, 1.7 mol, 1.0 equiv) was dissolved in methylene chloride (5 L, 0.34 M). 3-Chloroperoxybenzoic acid (488 g, 2.2 mol, 1.3 equiv) was added portionwise with cooling so that the reaction temperature did not rise above 34° C. After stirring for 1 h, the reaction mixture was quenched with 2 L of 1N aqueous NaOH and the product was extracted with methylene chloride. The combined organic layers were washed with saturated aqueous sodium bicarbonate, dried over MgSO4 and filtered. Heptane was added and the organic layer was evaporated to dryness, giving 246 g of 7-methylquinoline N-oxide (1-2) as a pink solid that was carried on without further purification. LRMS m/z (M+H)+ 160.1 found, 160.2 required.

Workup

  1. temperaturewith cooling so that the reaction temperature
  2. customdid not rise above 34° C
  3. customthe reaction mixture was quenched with 2 L of 1N aqueous NaOH
  4. extractionthe product was extracted with methylene chloride
  5. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. additionHeptane was added
  9. customthe organic layer was evaporated to dryness

Sources & evidence

ORD record
ord-24e989e873824270b0e8207c206fd3ba
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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