Allyl iodide → HCID 23369786, compound

HRID 1900786Notes

Reaction equation

HRID 1900786 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4]([CH3:15])=[C:5]([CH3:14])[C:6](=[O:13])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](I)[CH:23]=[CH2:24]>CN(C)C=O>[CH2:24]([O:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4]([CH3:15])=[C:5]([CH3:14])[C:6](=[O:13])[NH:7]2)[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 23369785HCID 23369785, compound

Product 1

HCID 23369786HCID 23369786, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

5-Hydroxy-3,4,8-trimethylcarbostyril (3.30 g, 16.3 mmol) was dissolved in N,N-dimethylformamide (100 ml), to which potassium carbonate (2.70 g, 19.6 mmol) and allyl iodide (2.91 g, 17.9 mmol) were added. The mixture was stirred in a bath of 75° C. for 8 hours. The reaction mixture was cooled, and the insoluble matter was removed by filtration. The filtrate was subjected to distillation under reduced pressure for removing the solvent. The residue was recrystallized from chloroform--n-hexane. As a result, 2.84 g of the title compound was obtained as pale yellow needles (71.7%).

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was cooled
  3. customthe insoluble matter was removed by filtration
  4. distillationThe filtrate was subjected to distillation under reduced pressure
  5. customfor removing the solvent
  6. customThe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-86b2263d3bf04578b752a0c1da720510
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…