Allyl bromide → HCID 21555662, compound

HRID 267221Notes

Reaction equation

HRID 267221 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CC(C)=O>[CH2:25]([O:16][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:15]=1)[CH:24]=[CH2:23]

Participants

5

Reactant 3

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

Product 1

HCID 21555662HCID 21555662, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A well-stirred mixture of 65.1 parts of ethyl-4-hydroxy-quinoline-2-carboxylate, 42 parts of anhydrous potassium carbonate, 38.4 parts of allyl bromide and 800 parts of acetone was boiled under reflux for 24 hours. The cooled reaction mixture was filtered to remove inorganic salts and acetone was removed by evaporation under reduced pressure. A solution of the residual brown oil in ether (360 parts) was washed successively with N-sodium hydroxide solution (3 portions each comprising 50 parts) and water (4 portions each of 100 parts), then dried over magnesium sulphate and evaporated to remove solvent. The resultant viscous oil crystallised on cooling and the crystals were recrystallised from light petroleum (60°-80°C) to yield 57.1 parts of ethyl 4-allyloxyquinoline-2-carboxylate as pale yellow needles, m.pt. 71°-72°C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto remove inorganic salts and acetone
  5. customwas removed by evaporation under reduced pressure
  6. washA solution of the residual brown oil in ether (360 parts) was washed successively with N-sodium hydroxide solution (3 portions each comprising 50 parts) and water (4 portions each of 100 parts),
  7. dry with materialthen dried over magnesium sulphate
  8. customevaporated
  9. customto remove solvent
  10. customThe resultant viscous oil crystallised
  11. temperatureon cooling
  12. customthe crystals were recrystallised from light petroleum (60°-80°C)

Sources & evidence

ORD record
ord-5ed6618fb27c4c57b605904f88256f16
Source dataset
uspto-grants-1976_03
Patent number
US03941793

Reaction notes

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