3-Chloro-1,2-propanediol → 5-(2,3-Dihydroxypropoxy)-3,4-dihydro-2(1H)-quinolinone

HRID 462046Notes

Reaction equation

HRID 462046 reaction equation
[Na].[OH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:13])[NH:8]2.[CH2:14]([OH:19])[CH:15]([OH:18])[CH2:16]Cl>C(O)C>[OH:18][CH:15]([CH2:14][OH:19])[CH2:16][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:13])[NH:8]2

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinoneHCID 5360545Sodium

Product 1

HCID 122853875-(2,3-Dihydroxypropoxy)-3,4-dihydro-2(1H)-quinolinoneYield 29.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.23 g of sodium metal was dissolved in 40 ml of ethanol, and 1.63 g of 5-hydroxy-3,4-dihydrocarbostyril and 1.1 g of glycerol α-monochlorohydrin were added to the resulting solution followed by refluxing the mixture for 6 hours. After allowing the mixture to cool, the precipitated crystals were filtered, and the filtrate was concentrated to dryness. The residue thus obtained was extracted with 100 ml of chloroform, and the extract was washed with a 5% aqueous sodium hydroxide solution and then water and then dried over anhydrous sodium sulfate. The chloroform was then removed by distillation and the resulting residue was recrystallized from ethanol to give 0.7 g of 5-(2,3-dihyroxy)propoxy-3,4-dihydrocarbostyril as a colorless amorphous solid having a melting point of 173° - 175° C.

Workup

  1. temperatureby refluxing the mixture for 6 hours
  2. temperatureto cool
  3. filtrationthe precipitated crystals were filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue thus obtained
  6. extractionwas extracted with 100 ml of chloroform
  7. washthe extract was washed with a 5% aqueous sodium hydroxide solution
  8. dry with materialwater and then dried over anhydrous sodium sulfate
  9. customThe chloroform was then removed by distillation
  10. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a9b3e3f3fa054fea92ce0693bed2ab1d
Source dataset
uspto-grants-1977_12
Patent number
US04065456

Reaction notes

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