Boron trifluoride etherate → 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

HRID 1380140Notes

Reaction equation

HRID 1380140 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10](=[O:24])[NH:11]2)(=[O:5])[CH3:4].B(F)(F)F.CCOCC>C(Cl)Cl>[Br:1][CH2:4][C:3]([C:6]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10](=[O:24])[NH:11]2)=[O:5]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 24408BromineHCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

Product 1

HCID 116678678-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinolineYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.8 g of bromine in 30 ml of methylene chloride is added dropwise to a refluxing solution of 13 g of 5-acetyl-8-benzyloxycarbostyril and 7.56 g of boron trifluoride etherate in 170 ml of methylene chloride, and the mixture is refluxed for 30 minutes under heating. The mixture is concentrated under reduced pressure to remove solvent. The residue is made alkaline with an aqueous 10% potassium carbonate solution, and the resultant precipitates are collected by filtration. The crystals are recrystallized from a mixture of chloroform and methanol. 12.51 g of 5-bromoacetyl-8-benzyloxycarbostyril are obtained as pale yellow needles. Yield: 75.7%

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. temperatureunder heating
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customto remove solvent
  5. customthe resultant precipitates
  6. filtrationare collected by filtration
  7. customThe crystals are recrystallized from a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-f2df55be8f514b14bdd13d0a1d6f1fa2
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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