Potassium Carbonate → HCID 54545512, compound

HRID 1900856Notes

Reaction equation

HRID 1900856 reaction equation
[CH:1]([C:4]1[C:5](=[O:16])[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([OH:14])[CH:10]=[CH:9][C:8]=2[CH3:15])([CH3:3])[CH3:2].[CH2:17](Br)[CH:18]=[CH:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl.O>CN(C)C=O>[CH2:17]([O:14][C:11]1[CH:10]=[CH:9][C:8]([CH3:15])=[C:7]2[C:12]=1[CH:13]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:16])[NH:6]2)[CH:18]=[CH:19][CH3:20]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 22418719Chloroform waterHCID 23369698HCID 23369698, compound

Product 1

HCID 54545512HCID 54545512, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-Isopropyl-5-hydroxy-8-methyl-1,2-dihydrocarbostyril (2.2 g, 10.13 mmol) was dissolved in dimethylformamide (25 ml). Crotylbromide (1.22ml, 12.11 mmol) and potassium carbonate (2.8 g, 20.26 mmol) were added to the solution, and the mixture was stirred at 70° C. for 2.5 hours. After the mixture was cooled, chloroform-water was added for phase separation. The organic phase was washed with water, and saturated aqueous sodium chloride solution in this order, and dried. The solvent was distilled off under reduced pressure, and the residue was recrystallized from chloroform-n-hexane. As a result, 1.88 g of the title compound was obtained as colorless needles (68%).

Workup

  1. temperatureAfter the mixture was cooled
  2. washThe organic phase was washed with water, and saturated aqueous sodium chloride solution in this order
  3. customdried
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was recrystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-21f05c2f07bc49ae8363f98c3d73a0e1
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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