Epichlorohydrin → 5-(Oxiran-2-ylmethoxy)quinoline

HRID 1654078Notes

Reaction equation

HRID 1654078 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[H-].[Na+].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>CN(C=O)C>[O:18]1[CH2:17][CH:16]1[CH2:14][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 135441757Quinolin-5-ol

Product 1

HCID 112178995-(Oxiran-2-ylmethoxy)quinolineYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In 20 ml of dried DMF was dissolved 1 g of 5-hydroxyquinoline, and 0.28 g of sodium hydride (60% content) was then added thereto, followed by heating with stirring at 50° C. for 30 minutes. Afterward, 1.92 g of epichlorohydrin was further added to the reaction liquid and the latter was then heated with stirring at 90° C. for 3 hours, and the solvent was distilled off under reduced pressure. Water was then added to the residue, and the liquid was extracted with chloroform. The chloroform extract was then decolored and purified with active carbon, then was dried with anhydrous sodium sulfate, and was distilled off. The residue was then purified through a silica gel column chromatograph by the use of an effluent solvent of chloroform:methanol=100:1, so that 0.88 g of 5-(2,3-epoxypropoxy)quinoline was obtained in an oily state.

Workup

  1. additionwas then added
  2. temperatureby heating
  3. temperaturethe latter was then heated
  4. stirringwith stirring at 90° C. for 3 hours
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionWater was then added to the residue
  7. extractionthe liquid was extracted with chloroform
  8. extractionThe chloroform extract
  9. custompurified with active carbon
  10. dry with materialwas dried with anhydrous sodium sulfate
  11. distillationwas distilled off
  12. customThe residue was then purified through a silica gel column chromatograph by the use of an effluent solvent of chloroform

Sources & evidence

ORD record
ord-870861b4b18744f29ac13f2cdb081cef
Source dataset
uspto-grants-1995_04
Patent number
US05405843

Reaction notes

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