Ethanol → 7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE

HRID 1750123Notes

Reaction equation

HRID 1750123 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2N[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.C([O-])([O-])=O.[K+].[K+].[CH3:24][CH2:25]O>O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][O:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:24]=[CH:25][C:7](=[O:9])[NH:8]2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 136166402H-Benzimidazol-2-one, 1,3-dihydro-5-hydroxy-

Product 1

HCID 107563157-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONEYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of intermediate 38 (253 mg, 1.68 mmol), 1,4-dibromobutane (0.6 mL, 5.04 mmol) and anhydrous K2CO3 (232 mg, 1.68 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 NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc=4:1) to give 7-(4-bromobutoxy)quinolin-2(1H)-one (intermediate 48) (120 mg, 25%) as a yellow solid.

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=4:1)

Sources & evidence

ORD record
ord-c82a4273eac4450dbbb6f6468cf0431a
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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