2-Hydroxyquinoline → HCID 64106163, compound

HRID 1916199Notes

Reaction equation

HRID 1916199 reaction equation
[H-].[Na+].CN(C)C=O.[NH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:18].Br[CH2:20][CH2:21][CH2:22][CH2:23][Cl:24]>O>[Cl:24][CH2:23][CH2:22][CH2:21][CH2:20][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:18]

Participants

6

Reactant 4

HCID 60382-HydroxyquinolineHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 64106163HCID 64106163, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.30 g of sodium hydride (60% oily) was added to a dimethylformamide (20 ml) solution of 1.0 g of 1H-quinolin-2-one while being stirred under ice-cooling and stirred at room temperature for 0.5 hour, and after that 1.6 ml of 1-bromo-4-chlorobutane was added and stirred at room temperature for 14 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate and, after washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), and 1.02 g of 1-(4-chlorobutyl)-1H-quinolin-2-one was obtained in the form of colorless oil.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for 0.5 hour
  3. stirringstirred at room temperature for 14 hours
  4. extractionwas then extracted with ethyl acetate
  5. washafter washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-db9eec7e97464fcd9a2db13aedb01056
Source dataset
uspto-grants-2013_12
Patent number
US08618109B2

Reaction notes

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