2-Methylquinoline → Chromone

HRID 1090781Notes

Reaction equation

HRID 1090781 reaction equation
C([C:6]1[O:7][C:8]2[CH:16]=[C:15](O)[CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)(OCC)=O.CC1C=CC2C(=CC=CC=2)N=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CC(C)=O>[O:12]=[C:10]1[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[O:7][CH:6]=[CH:11]1

Participants

6

Reactant 3

HCID 70602-MethylquinolineHCID 11430Potassium CarbonateHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Product 1

HCID 10286Chromone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5g (6.41 mmoles) of 2-carboethoxy-7- hydroxy-4-oxo-4H-1-benzopyran, 1.82g (6.41 mmoles) of 2-3-chloromethylphenoxy)methylquinoline and 0.886 g of potassium carbonate in 12 ml of dimethylformamide and 96 ml of acetone is refluxed for 2 days, cooled, concentrated in vacuo and the residue taken up in water and is extracted into ethyl acetate. The solution is concentrated and the crude product is recrystallized from ethyl acetate to give 0.585g of 2-carboethoxy-7-(3-quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran as a pale yellow solid having an m.p. of 123°-24° C.

Workup

  1. temperatureis refluxed for 2 days
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. extractionis extracted into ethyl acetate
  5. concentrationThe solution is concentrated
  6. customthe crude product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-89a420d56def4ec3af3d908b561848dc
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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