1,3-Dibromopropane → 7-(3-Bromopropoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1750066Notes

Reaction equation

HRID 1750066 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]Br.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH2:15][CH2:16][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 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 299270147-(3-Bromopropoxy)-3,4-dihydroquinolin-2(1H)-oneYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7-hydroxy-3,4-dihydroquinolin-2(1H)-one (195 mg, 1.2 mmol), 1,3-dibromopropane (960 mg, 4.8 mmol) and anhydrous K2CO3 (166 mg, 1.2 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 aq 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-(3-bromopropoxy)-3,4-dihydroquinolin-2(1H)-one (intermediate 3) (300 mg, 88%) as a white solid. HPLC: 99%, RT 2.775 min. MS (ESI) m/z 284.0 [M+H]+.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with saturated aq 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-7aa047d8dc7f4ae2a947b45abc0978ff
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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