Epichlorohydrin → 5-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-one

HRID 1979764Notes

Reaction equation

HRID 1979764 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[OH-].[Na+].[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl>CO>[O:19]1[CH2:18][CH:17]1[CH2:15][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinone

Product 1

HCID 128994235-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.4 Grams of 5-hydroxy-3,4-dihydrocarbostyril and 3.7 g of sodium hydroxide were added into 100 ml of methanol and stirred at 40°-50° C. for 3 hours, then 150 ml of epichlorohydrin was added thereto and heated under refluxing condition for 5 hours. The reaction mixture was concentrated under a reduced pressure to dryness and the residue thus obtained was recrystallized from methanol-water (1:1) to obtain 18.5 g of 5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril having the melting of 172°-173° C. as in the form of coloress amorphous crystals.

Workup

  1. temperatureheated
  2. temperatureunder refluxing condition for 5 hours
  3. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness
  4. customthe residue thus obtained
  5. customwas recrystallized from methanol-water (1:1)

Sources & evidence

ORD record
ord-317ac126b9344d77b99223aa3a40f385
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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