Allyl iodide → HCID 23369687, compound

HRID 1900848Notes

Reaction equation

HRID 1900848 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](I)[CH:24]=[CH2:25]>CN(C)C=O>[CH2:25]([O: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)[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 23369698HCID 23369698, compound

Product 1

HCID 23369687HCID 23369687, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5-Hydroxy-3-isopropyl-8-methylcarbostyril (1.60 g, 7.37 mmol) was dissolved in dimethylformamide (30 ml), to which potassium carbonate (2.50 g, 18.1 mmol) and allyl iodide (0.71 ml, 7.76 mmol) were added. The mixture was stirred at 70° C. for 90 minutes. The reaction mixture was condensed under reduced pressure. 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-ether to obtain 1.85 g of the title compound as pale yellow powdery crystals (97.9%).

Workup

  1. additionwere added
  2. customcondensed under reduced pressure
  3. extractionThe resultant residue was extracted from chloroform-water
  4. washThe organic phase was washed with saturated aqueous NaCl solution
  5. customdried
  6. customcondensed under reduced pressure
  7. customThe residue was recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-a75fd44339d8497aa43f4c57e7703415
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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