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

HRID 1750068Notes

Reaction equation

HRID 1750068 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

6

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 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7-hydroxy-3,4-dihydroquinolin-2(1H)-one (163 mg, 1.0 mmol), 1,4-dibromobutane (0.36 mL, 3.0 mmol) and anhydrous K2CO3 (138 mg, 1.0 mmol) were dissolved in EtOH and the solution was heated to reflux overnight. The solution was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc=2:1) to give 7-(4-bromobutoxy)-3,4-dihydroquinolin-2(1H)-one (intermediate 4) (220 mg, 74%) as a white solid. mp: 106-109° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel column (elution with PE/EtOAc=2:1)

Sources & evidence

ORD record
ord-034bfea39a744b0bbec0fafd3938a23c
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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