3-Chloro-1,2-propanediol → 8-(2,3-Dihydroxy)propoxy-3,4-dihydrocarbostyril

HRID 462048Notes

Reaction equation

HRID 462048 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:14])[CH2:10][CH2:9]2.[CH2:15]([OH:20])[CH:16]([OH:19])[CH2:17]Cl>CO>[OH:19][CH:16]([CH2:15][OH:20])[CH2:17][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:14])[CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 14797Potassium HydroxideHCID 2682398-Hydroxy-3,4-dihydroquinolin-2(1h)-one

Product 1

HCID 213903498-(2,3-Dihydroxy)propoxy-3,4-dihydrocarbostyrilYield 33.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.8 g of potassium hydroxide was dissolved in 50 ml of methanol, and 1.63 g of 8-hydroxy-3,4-dihydrocarbostyril and 1.4 g of glycerol α-monochlorohydrin were added to the resulting solution followed by refluxing the mixture for 3 hours. The raction mixture was then concentrated to dryness, and the resulting residue was extracted with 50 ml of chloroform. The extract was washed with a 2% 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 0.8 g of 8-(2,3-dihydroxy)propoxy-3,4-dihydrocarbostyril as a light yellow amorphous solid having a melting point of 182° - 184° C.

Workup

  1. temperatureby refluxing the mixture for 3 hours
  2. concentrationThe raction mixture was then concentrated to dryness
  3. extractionthe resulting residue was extracted with 50 ml of chloroform
  4. washThe extract was washed with a 2% aqueous sodium hydroxide solution
  5. dry with materialwater, and then dried over anhydrous sodium sulfate
  6. customThe chloroform was then removed by distillation
  7. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9e1a08fd7f5b4c0ca324613a5ce25eb5
Source dataset
uspto-grants-1977_12
Patent number
US04065456

Reaction notes

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