Water → HCID 18347802, compound

HRID 228838Notes

Reaction equation

HRID 228838 reaction equation
[OH:1][C:2]1[C:3]([CH3:12])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH2:13]>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:3]([CH:12]=[O:13])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 962WaterHCID 5943942-methylquinolin-3-ol

Product 1

HCID 18347802HCID 18347802, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

3-Hydroxy-2-methyl-quinoline (0.46 g) was suspended in xylene (30 ml), zelene dioxide (2.55 g) was added to the suspension, and the mixture was stirred at 130° C. for 30 min. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give 3-hydroxyquinoline-2-carbaldehyde (124 mg, yield 25%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was then washed with water
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-debe0c80da554774ab6e75ed863675dc
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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