Allyl bromide → Ethyl 4-allyloxyquinoline-2-carboxylate

HRID 1580066Notes

Reaction equation

HRID 1580066 reaction equation
[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=1.[CH2:17](Br)[CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:19]([O:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=1)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 178469285HCID 178469285, compound

Product 1

HCID 21555662Ethyl 4-allyloxyquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxyquinaldic acid, ethyl ester (16 g), allyl bromide (22.5 g) and anhydrous potassium carbonate (30 g) in dimethylformamide (300 ml) were stirred and heated on a steam bath for 20 hours. The mixture was filtered, the filtrate was evaporated and the residue was crystallised from a mixture of ethyl acetate and light petroleum (b.p. 60°-80°) to give 4-allyloxyquinaldic acid, ethyl ester.

Workup

  1. temperatureheated on a steam bath for 20 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customthe residue was crystallised from a mixture of ethyl acetate and light petroleum (b.p. 60°-80°)

Sources & evidence

ORD record
ord-8960fa4fc45e452ba0d4b43c8d217235
Source dataset
uspto-grants-1976_01
Patent number
US03932416

Reaction notes

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