Epichlorohydrin → 5-(2,3-Epoxy)propoxycarbostyril

HRID 1606522Notes

Reaction equation

HRID 1606522 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:14])[NH:9]2.[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl>O>[CH2:18]1[O:19][CH:17]1[CH2:15][O:3][C:4]1[C:5]2[CH:6]=[CH:7][C:8]([NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:14]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 53822135-hydroxyquinolin-2(1H)-one

Product 1

HCID 215436385-(2,3-Epoxy)propoxycarbostyril

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.6 g of sodium hydroxide was dissolved in 40 ml of water, and 2.0 g of 5-hydroxycarbostyril and 2.5 g of epichlorohydrin were added to the solution. The mixture was stirred at a temperature of from 60° to 70°C for 5 hours followed by cooling to precipitate the product. The precipitated crystals were washed with water, dissolved in ethanol and then subjected to thin layer chromatography using acetone as an eluate to obtain two spots having a Rf value of 0.58 and 0.65, respectively, The spot having a Rf value of 0.58 was extracted with ethanol and crystallized to obtain 5-(2,3-epoxy)propoxycarbostyril which was used as the starting material in Examples 1 and 2. The spot having a Rf value of 0.65 was worked up in the same manner as described above to obtain 5-(2-hydroxy-3-chloro)propoxycarbostyril which was used as the starting material in Example 3.

Workup

  1. temperatureby cooling
  2. customto precipitate the product
  3. washThe precipitated crystals were washed with water
  4. dissolutiondissolved in ethanol
  5. customto obtain two spots
  6. extractionwas extracted with ethanol
  7. customcrystallized

Sources & evidence

ORD record
ord-ab0ca3d55ac54e0c883f262116c1f5bd
Source dataset
uspto-grants-1976_04
Patent number
US03953456

Reaction notes

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