1,4-Dibromobutane → 7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

HRID 1084696Notes

Reaction equation

HRID 1084696 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 105420647-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinoneYield 68.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4.06 g of potassium carbonate with 400 ml of water was added 40 g of 7-hydroxy-3,4-dihydrocarbostyril and 158 g of 1,4-dibromobutane, then the mixture was refluxed for 3 hours. The reaction mixture thus obtained was extracted with dichloromethane, dried with anhydrous magnesium sulfate, then the solvent was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane), and recrystallized from n-hexane-ethanol to yield 50 g of 7-(4-bromobutoxy)-3,4-dihydrocarbostyril.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe reaction mixture thus obtained
  3. extractionwas extracted with dichloromethane
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customThe residue thus obtained
  7. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane)
  8. customrecrystallized from n-hexane-ethanol

Sources & evidence

ORD record
ord-7608edafb5cc40269066b6c51abaa41d
Source dataset
uspto-grants-1991_04
Patent number
US05006528

Reaction notes

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