Acetone → 8-(2-Propynyloxy)-5-hydroxy-3,4-dihydrocarbostyril

HRID 2057450Notes

Reaction equation

HRID 2057450 reaction equation
[CH3:1][C:2]([CH3:4])=O.[OH:5][C:6]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:17])[NH:11]2.C(=O)([O-])[O-].[K+].[K+].C(Br)C#C>O>[CH2:4]([O:16][C:13]1[CH:14]=[CH:15][C:6]([OH:5])=[C:7]2[C:12]=1[NH:11][C:10](=[O:17])[CH2:9][CH2:8]2)[C:2]#[CH:1]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 1515652(1H)-Quinolinone, 3,4-dihydro-5,8-dihydroxy-

Product 1

HCID 127517408-(2-Propynyloxy)-5-hydroxy-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 liters of acetone and 500 ml of water were added to 150 g of 5,8-dihydroxy-3,4-dihydrocarbostyril, and 138 g of potassium carbonate and 150 g of 2-propynyl bromide were further added thereto. The resulting mixture was heated while refluxing for 3 hours on a water bath. After completion of the reaction, the acetone and the 2-propynyl bromide were evaporated under reduced pressure, and the residue was made acidic with concentrated hydrochloric acid. The mixture was extracted with chloroform, and the chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform was evaporated under reduced pressure, and the residual crystals were recrystallized from isopropanol-diethyl ether to obtain 110 g of 8-(2-propynyloxy)-5-hydroxy-3,4-dihydrocarbostyril having a melting point of 141°-142° C.

Workup

  1. additionwere further added
  2. temperatureThe resulting mixture was heated
  3. temperaturewhile refluxing for 3 hours on a water bath
  4. customAfter completion of the reaction
  5. customthe acetone and the 2-propynyl bromide were evaporated under reduced pressure
  6. extractionThe mixture was extracted with chloroform
  7. washthe chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe chloroform was evaporated under reduced pressure
  10. customthe residual crystals were recrystallized from isopropanol-diethyl ether

Sources & evidence

ORD record
ord-5d9184b5b0104c619aba21e06fb0b5bb
Source dataset
uspto-grants-1980_07
Patent number
US04210753

Reaction notes

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