1-Bromo-3-chloropropane → 6-(3-Chloropropoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1913891Notes

Reaction equation

HRID 1913891 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>C(#N)C.C(Cl)(Cl)Cl>[Cl:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 110428286-(3-Chloropropoxy)-3,4-dihydroquinolin-2(1H)-oneYield 68%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 6-hydroxy-3,4-dihydroquinolin-2(1H)-one (50 g), cesium carbonate (150 g) and 1-bromo-3-chloropropane (58 g) in acetonitrile (300 mL) was stirred at 110° C. for 4 hours. The reaction mixture was cooled to room temperature, diluted with chloroform and filtered to remove insoluble materials. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform→chloroform/methanol=4/1), and the resulting solid was subjected to recrystallization from ethanol to give the titled compound (42 g, 68%) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto remove insoluble materials
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform→chloroform/methanol=4/1)
  6. customthe resulting solid was subjected to recrystallization from ethanol

Sources & evidence

ORD record
ord-895a848c53b64866843b6dabaca4a96d
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

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