Benzyl Bromide → HCID 21555704, compound

HRID 267223Notes

Reaction equation

HRID 267223 reaction equation
[CH2:1]([C:4]1[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O>[CH2:1]([C:4]1[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178439523HCID 178439523, compound

Product 1

HCID 21555704HCID 21555704, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A well-stirred mixture of 5 parts of ethyl 3-n-propyl-4-hydroxyquinoline-2-carboxylate, 3 parts of anhydrous potassium carbonate and 3.3 parts of benzyl bromide in anhydrous acetone was boiled under reflux for 16 hours, filtered to remove inorganic salts, and evaporated to remove solvent. A solution of the residual oil in 75 parts of ether, after being washed with N.sodium hydroxide (2 portions each comprising 25 parts) and then water (4 portions each of 40 parts) was dried over magnesium sulphate and evaporated to yield 6.4 parts of crude ethyl 3-n-propyl-4-benzyloxyquinoline-2-carboxylate as a very pale yellow oil.

Workup

  1. temperatureunder reflux for 16 hours
  2. filtrationfiltered
  3. customto remove inorganic salts
  4. customevaporated
  5. customto remove solvent
  6. washA solution of the residual oil in 75 parts of ether, after being washed with N
  7. dry with materialsodium hydroxide (2 portions each comprising 25 parts) and then water (4 portions each of 40 parts) was dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-7c9266ba846c4d41b6c6a7ccb101663a
Source dataset
uspto-grants-1976_03
Patent number
US03941793

Reaction notes

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