Potassium Carbonate → HCID 23369821, compound

HRID 1900851Notes

Reaction equation

HRID 1900851 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:14]([CH3:16])[CH3:15])[C:6](=[O:13])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[C:25]([CH3:27])[CH3:26]>CN(C)C=O>[CH:14]([C:5]1[C:6](=[O:13])[NH:7][C:8]2[C:3]([CH:4]=1)=[C:2]([O:1][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH:11]=[CH:10][C:9]=2[CH3:12])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 23369698HCID 23369698, compound

Product 1

HCID 23369821HCID 23369821, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5-HYdroxy-3-isopropyl-8-methylcarbostyril (1.50 g, 6.91 mmol) was dissolved in dimethylformamide (30 ml). To the solution, potassium carbonate (3.00 g, 21.7 mmol) and prenyl bromide (0.90 ml, 7.67 mmol) were added, and the mixture was stirred at 70° C. for 7 hours. The reaction mixture was condensed under reduced pressure, and the resultant residue was extracted from chloroform-water. The organic phase was washed with saturated aqueous NaCl solution, dried, and condensed under reduced pressure. The residue was recrystallized from chloroform-ethyl acetate to obtain 1.85 g of the title compound as pale yellow needles (97.9%).

Workup

  1. customcondensed under reduced pressure
  2. extractionthe resultant residue was extracted from chloroform-water
  3. washThe organic phase was washed with saturated aqueous NaCl solution
  4. customdried
  5. customcondensed under reduced pressure
  6. customThe residue was recrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-f636cca6c251429e80e2ec34ba327941
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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