5-Chloro-8-hydroxyquinoline → HCID 18947641, compound

HRID 1769261Notes

Reaction equation

HRID 1769261 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][CH:29]=[CH2:30])=[O:22]>CS(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:20][C:21]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][CH:29]=[CH2:30])=[O:22])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 28175-Chloro-8-hydroxyquinolineHCID 11430Potassium CarbonateHCID 18947637HCID 18947637, compound

Product 1

HCID 18947641HCID 18947641, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.78 g (0.021 mol) of 5-chloro-8-hydroxyquinoline and 2.91 g (0.021 mol) of potassium carbonate are heated at 60° C. in 100 ml of dimethylsulfoxide (DMSO) for 30 minutes. The mixture is allowed to cool again to room temperature, 5.0 g (0.021 mol) of 3-(allyloxy)propyl bromoacetate are then added dropwise and the solution is subsequently heated at 90° C. for 4 hours. The DMSO is then distilled off in vacuo, the residue is taken up in ethyl acetate and the solution is washed with water and 5 percent strength sodium hydroxide solution. The organic phase is dried over magnesium sulfate, the desiccant is filtered off and the solvent is stripped off under reduced pressure. After recrystallization of the residue from n-heptane, 5.4 g (76.3% of theory) of 3-(allyloxy)propyl

Workup

  1. temperaturethe solution is subsequently heated at 90° C. for 4 hours
  2. distillationThe DMSO is then distilled off in vacuo
  3. washthe solution is washed with water and 5 percent strength sodium hydroxide solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationthe desiccant is filtered off
  6. customAfter recrystallization of the residue from n-heptane, 5.4 g (76.3% of theory) of 3-(allyloxy)propyl

Sources & evidence

ORD record
ord-cdba80a7d3494f7eb144012db6ee60da
Source dataset
uspto-grants-1995_01
Patent number
US05380852

Reaction notes

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