1,3-Dibromopropane → 7-(3-bromopropoxy)quinolin-2(1H)-one

HRID 1750102Notes

Reaction equation

HRID 1750102 reaction equation
C(OC1C=CC=CC=1N1CCCN(C[CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:31]=[C:30]3[C:25]([CH:26]=[CH:27][C:28](=[O:32])[NH:29]3)=[CH:24][CH:23]=2)CC1)C.[Br:33]CCCBr.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:33][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][C:28](=[O:32])[NH:29]2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 666335847-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one

Product 1

HCID 299750407-(3-bromopropoxy)quinolin-2(1H)-oneYield 55%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of intermediate 14 (193 mg, 1.2 mmol), 1,3-dibromopropane (0.37 mL, 3.6 mmol) and anhydrous K2CO3 (166 mg, 1.2 mmol) was 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)quinolin-2(1H)-one (intermediate 32) (185 mg, 55%) as a white solid.

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-92b51a7e9eaf485091543e8018c38da4
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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