Acetone → 5-Hydroxy-8-(2-methoxyethoxy)-3,4-dihydrocarbostyril

HRID 2057448Notes

Reaction equation

HRID 2057448 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:13])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].CC(C)=O.[CH3:24][O:25][CH2:26][CH2:27]Br>O>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:27][CH2:26][O:25][CH3:24])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:13])[NH:7]2

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1515652(1H)-Quinolinone, 3,4-dihydro-5,8-dihydroxy-

Product 1

HCID 127517385-Hydroxy-8-(2-methoxyethoxy)-3,4-dihydrocarbostyrilYield 52.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

21.6 g of 5,8-dihydroxy-3,4-dihydrocarbostyril and 19.9 g of potassium carbonate were added to a mixture comprising 480 ml of acetone and 120 ml of water, and the resulting mixture was stirred while refluxing for 30 minutes. 76 g of 2-methoxyethyl bromide was then added thereto followed by stirring while refluxing for 8 hours. The solvent was evaporated, and water was added to the residue. The mixture was extracted with diethyl ether. The aqueous layer was rendered acidic with hydrochloric acid and then extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, and the chloroform evaporated to obtain 15 g of 5-hydroxy-8-(2-methoxyethoxy)-3,4-dihydrocarbostyril as a black oily substance.

Workup

  1. temperaturewhile refluxing for 30 minutes
  2. stirringby stirring
  3. temperaturewhile refluxing for 8 hours
  4. customThe solvent was evaporated
  5. additionwater was added to the residue
  6. extractionThe mixture was extracted with diethyl ether
  7. extractionextracted with chloroform
  8. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  9. customthe chloroform evaporated

Sources & evidence

ORD record
ord-2075a6528d144450999ce2ae688621e6
Source dataset
uspto-grants-1980_07
Patent number
US04210753

Reaction notes

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