Hydrogen Peroxide → 6-Methoxyquinoline N-oxide

HRID 1472704Notes

Reaction equation

HRID 1472704 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[OH:13]O.[OH-].[Na+]>CC(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([O-:13])=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 148606-Methoxyquinoline

Product 1

HCID 2538216-Methoxyquinoline N-oxideYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-methoxyquinoline (2.00 g, 12.6 mmol) in AcOH (10 mL) was added H2O2 (30% in water, 1.9 mL, 18.9 mmol), the mixture was heated to 70° C. for 21 hours. The mixture was basified with 2M NaOH to pH 8-9 and extracted with CH2Cl2 (200 mL), the combined organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by silica gel column (EtOAc/MeOH=10/1) to give 6-methoxyquinoline 1-oxide (1.20 g, 55%) as a solid.

Workup

  1. extractionextracted with CH2Cl2 (200 mL)
  2. washthe combined organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by silica gel column (EtOAc/MeOH=10/1)

Sources & evidence

ORD record
ord-4494c54ecd1c498fb329157f9df2fae5
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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