Chloroform → HCID 19978296, compound

HRID 1449490Notes

Reaction equation

HRID 1449490 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.C(Cl)(Cl)Cl>CN(C)C=O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 178515546HCID 178515546, compound

Product 1

HCID 19978296HCID 19978296, compoundYield 6,424.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-hydroxyquinoline (0.29 g, 2.0 mmoles) was dissolved in 4 ml of dimethylformamide, 60% sodium hydride (80 mg, 2.0 mmoles) was added to the solution, and the mixture was stirred at 60° C. for 30 minutes and then cooled to room temperature. 1,4-dibromobutane (2.16 g, 10 mmoles) was further added, and the resulting mixture was stirred at 60° C. for 4 hours. After chloroform was added to the reaction mixture, insolubles were removed by filtration, the filtrate was washed with water, and the solvent was evaporated. The residue thus obtained was purified by chromatography on a silica gel column to give 36 g (yield 64%) of the title compound as an oil.

Workup

  1. temperaturecooled to room temperature
  2. stirringthe resulting mixture was stirred at 60° C. for 4 hours
  3. customwere removed by filtration
  4. washthe filtrate was washed with water
  5. customthe solvent was evaporated
  6. customThe residue thus obtained
  7. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-d6f9f36330ed48018a9380513e0f3039
Source dataset
uspto-grants-1997_02
Patent number
US05599815

Reaction notes

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