Hydrogen Peroxide → 2-Hydroxyquinoline

HRID 2222390Notes

Reaction equation

HRID 2222390 reaction equation
[OH:1]O.C([C:5]1[C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1CCCCCCC)=O>CCO.[OH-].[Na+]>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:5][C:6]1=[O:1]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 99001373-formyl-2-heptyl-4(1H)-quinolone

Product 1

HCID 60382-HydroxyquinolineYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Aqueous hydrogen peroxide (27.5 wt % solution in water, 145 μl) was added to a solution of 3-formyl-2-heptyl-4(1H)-quinolone (1 mmol) in EtOH (3 ml) and 1M NaOH solution (1.0 ml) under nitrogen, and the mixture was stirred at room temperature for 6 hours. The precipitate was removed by filtration, air dried and crystallised from EtOAc to give 2-heptyl-3-hydroxy-4(1M-quinolone in 70% yield as off-white needles, mp 195-197° C.

Workup

  1. customThe precipitate was removed by filtration, air
  2. customdried
  3. customcrystallised from EtOAc

Sources & evidence

ORD record
ord-177461980767419d9ae305a69112f079
Source dataset
uspto-grants-2008_05
Patent number
US07371779B2

Reaction notes

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