3-Chloro-1,2-propanediol → HCID 21390340, compound

HRID 462043Notes

Reaction equation

HRID 462043 reaction equation
[OH-].[K+].[CH3:3][N:4]1[C:14]2[C:9](=[C:10]([OH:15])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:5]1=[O:6].[CH2:16]([OH:21])[CH:17]([OH:20])[CH2:18]Cl>CO>[CH3:3][N:4]1[C:14]2[C:9](=[C:10]([O:15][CH2:18][CH:17]([OH:20])[CH2:16][OH:21])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 14797Potassium HydroxideHCID 1822025-Hydroxy-1-methyl-3,4-dihydroquinolin-2-one

Product 1

HCID 21390340HCID 21390340, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 g of potassium hydroxide was dissolved in 80 ml of methanol, and 4.8 g of 1-methyl-5-hydroxy-3,4-dihydrocarbostyril and 4.0 g of glycerol α-monochlorohydrin were added to the resulting solution followed by refluxing the mixture for 4 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 120 ml of chloroform, and the extract was washed with a 5% aqueous potassium 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 ethyl acetate to give 1.5 g of 1-methyl-5-(2,3-dihydroxy)propoxy-3,4-dihydrocarbostyril as a colorless amorphous solid having a melting point of 120° - 121° C.

Workup

  1. temperatureby refluxing the mixture for 4 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 120 ml of chloroform
  7. washthe extract was washed with a 5% aqueous potassium 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 ethyl acetate

Sources & evidence

ORD record
ord-a204e0ed460b49758d50c1b976f8c1b4
Source dataset
uspto-grants-1977_12
Patent number
US04065456

Reaction notes

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