Hydrogen Peroxide → 6-Methoxyquinoline N-oxide

HRID 493421Notes

Reaction equation

HRID 493421 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>C(O)(=O)C>[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

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 148606-Methoxyquinoline

Product 1

HCID 2538216-Methoxyquinoline N-oxideYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

6-Methoxy quinoline (15 g, 0.094 mol) was dissolved in acetic acid (97 ml) and treated with hydrogen peroxide (37 ml). The mixture was stirred to 100° C. for 2 hours. After evaporation to dryness 100 ml of water was added to the residue until a precipitate appears. Filtration and washing with water gives a yellow precipitate that is dried under vacuum to yield 13.5 g of the title compound as a light yellow solid (82%). MS (m/e): 176.3 (M+H)+.

Workup

  1. customAfter evaporation to dryness 100 ml of water
  2. additionwas added to the residue until a precipitate
  3. filtrationFiltration
  4. washwashing with water
  5. customgives a yellow precipitate that
  6. customis dried under vacuum

Sources & evidence

ORD record
ord-7d4c626e781c45508d7b39a81a93de5c
Source dataset
uspto-grants-2009_05
Patent number
US07534891B2

Reaction notes

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