Epichlorohydrin → HCID 12751742, compound

HRID 1090694Notes

Reaction equation

HRID 1090694 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([OH:20])=[C:13]3[C:18]=2[NH:17][C:16](=[O:19])[CH2:15][CH2:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>C(O)C>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([O:20][CH2:27][CH:29]3[O:31][CH2:30]3)=[C:13]3[C:18]=2[NH:17][C:16](=[O:19])[CH2:15][CH2:14]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 127517378-(Benzyloxy)-5-hydroxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 12751742HCID 12751742, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-Phenylmethoxy-3,4-dihydro-5-hydroxycarbostyril (32.5 g) was dissolved in ethanol (300 mL). Potassium carbonate (25 g) and epichlorohydrin (45 g) were added to the solution, and the mixture heated under reflux for four hours. After cooling, the ethanol was evaporated and water added. The aqueous solution was then extracted with methylene chloride, the resulting solution was washed with water, dried over sodium sulfate and the methylene chloride was evaporated under reduced pressure. The residue was worked up with diisopropyl ether (10 mL), yielding 35 g of 8-phenylmethoxy-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril, m.p. 106°-108° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for four hours
  3. temperatureAfter cooling
  4. customthe ethanol was evaporated
  5. additionwater added
  6. extractionThe aqueous solution was then extracted with methylene chloride
  7. washthe resulting solution was washed with water
  8. dry with materialdried over sodium sulfate
  9. customthe methylene chloride was evaporated under reduced pressure

Sources & evidence

ORD record
ord-04e9234afdd143fe841d0f946c3c9ac2
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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