Hydrogen Peroxide → 8-Hydroxyquinoline N-oxide

HRID 1167190Notes

Reaction equation

HRID 1167190 reaction equation
[OH: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.ClCCl.[OH:15]O>C[Re](=O)(=O)=O.[O-2].[O-2].[Mn+4]>[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-:15])=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 19238-HydroxyquinolineHCID 6344Dichloromethane

Product 1

HCID 143128-Hydroxyquinoline N-oxideYield 97%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 178477782HCID 178477782, compoundCatalyst

Conditions

Temperature
25 °C

Procedure

59.74 g (411 mmol) of 8-hydroxyquinoline, 350 ml (822 mmol) of dichloromethane, 82.2 ml of 35% aqueous hydrogen peroxide solution and 0.52 g (2.5 mmol) of methylrhenium trioxide (MTO) are placed in a 1 l round-bottomed flask. The reaction mixture is stirred at ambient temperature (25° C.) for 24 h and then 80 ml of aqueous hydrogen peroxide solution and 0.32 g of manganese dioxide are successively added. The mixture is stirred for 1 h 30 and then separated by settling. The aqueous phase is extracted with dichloromethane (2×200 ml). The organic phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum to provide 64 g of 8-hydroxyquinoline N-oxide in the form of an organe-colored solid; M.p.=112° C. (Yield: 97%)

Workup

  1. stirringThe mixture is stirred for 1 h 30
  2. customseparated
  3. extractionThe aqueous phase is extracted with dichloromethane (2×200 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4a5b83736d134f5b9b096add3c599ff2
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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