Epichlorohydrin → 5-(2,3-Epoxypropoxy)-8-(2-propynyloxy)-3,4-dihydrocarbostyril

HRID 2057451Notes

Reaction equation

HRID 2057451 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3].[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:19]2[O:21][CH2:20]2)=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 127517408-(2-Propynyloxy)-5-hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 127517465-(2,3-Epoxypropoxy)-8-(2-propynyloxy)-3,4-dihydrocarbostyrilYield 68.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 78 g of 8-(2-propynyloxy)-5-hydroxy-3,4-dihydrocarbostyril were added 102 g of epichlorohydrin, 60 g of potassium carbonate and 600 ml of methanol, and the resulting mixture was heated while refluxing for 2.5 hours on a water bath. After completion of the reaction, the methanol was evaporated, and water was added to the residue followed by extracting with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure, and the residual crystals were recrystallized from isopropanol to obtain 67 g of 8-(2-propynyloxy)-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril having a melting point of 142°-143.5° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperaturewhile refluxing for 2.5 hours on a water bath
  3. customAfter completion of the reaction
  4. customthe methanol was evaporated
  5. additionwater was added to the residue
  6. extractionby extracting with chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe chloroform was evaporated under reduced pressure
  10. customthe residual crystals were recrystallized from isopropanol

Sources & evidence

ORD record
ord-84bd3102536a4d75ab172d31081d43bf
Source dataset
uspto-grants-1980_07
Patent number
US04210753

Reaction notes

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