Hydrogen Peroxide → 6-Chloro-7-methoxyquinoline 1-oxide

HRID 579333Notes

Reaction equation

HRID 579333 reaction equation
[OH:1]O.[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[CH:7]2>C(Cl)Cl.O=[Mn]=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N+:10]([O-:1])=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 867271546-Chloro-7-methoxyquinoline

Product 1

HCID 867271566-Chloro-7-methoxyquinoline 1-oxide

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round bottom flask, 6-chloro-7-methoxyquinoline was dissolved in DCM (25.8 mL) and MTO (0.051 g, 0.207 mmol) was added. The reaction mixture was capped and vented with a needle, then placed in an ice bath to cool. Once cool, hydrogen peroxide (0.633 mL, 10.33 mmol) was added drop-wise. When the addition was complete, the reaction mixture was removed from cooling, warmed to room temperature and stirred overnight (18 h). MnO2 (10 mg, 0.115 mmol) was added and the reaction mixture was stirred for an additional 2 h. The reaction mixture was filtered through celite, washing with DCM, then concentrated in vacuo to yield 6-chloro-7-methyoxyquinoline 1-oxide (1.036 g) MS [M+H+]=210.3.

Workup

  1. additionMTO (0.051 g, 0.207 mmol) was added
  2. customThe reaction mixture was capped
  3. customplaced in an ice bath
  4. temperatureto cool
  5. temperatureOnce cool
  6. additionWhen the addition
  7. customthe reaction mixture was removed
  8. temperaturefrom cooling
  9. stirringthe reaction mixture was stirred for an additional 2 h
  10. filtrationThe reaction mixture was filtered through celite
  11. washwashing with DCM
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08b1e63a24ed4945a959e4fa26f63dac
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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