Water → 2-Hydroxyquinoline

HRID 1586082Notes

Reaction equation

HRID 1586082 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([C:6](OC)=[C:7](OC(=O)C)[C:8](=[O:13])[N:9]2C)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[NH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 154351697-Amino-4-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl acetate

Product 1

HCID 60382-HydroxyquinolineYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.95 g of 7-amino-3-acetoxy-4-methoxy-1-methyl-2(1H)-quinolinone (3.6 mmol) in 20 ml of DMF were added 0.55 g of potassium carbonate (4.0 mmol) and 0.56 g of methyl iodide (4.0 mmol) and stirred at room temperature for 1 hour. The reaction mixture was added to water and extracted with toluene, the organic layer was concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (hexane/ethyl acetate=1/1 as an eluent) gave 0.45 g of the title compound (9). (yield=45%)

Workup

  1. extractionextracted with toluene
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customPurification of the residue by column chromatography on silica gel (hexane/ethyl acetate=1/1 as an eluent)

Sources & evidence

ORD record
ord-8b24bacb03204ddc82e1be7e4194bdb9
Source dataset
uspto-grants-1999_08
Patent number
US05942521

Reaction notes

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