Allyl iodide → 5-Allyloxy-3,8-dimethylcarbostyril

HRID 1900808Notes

Reaction equation

HRID 1900808 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]([CH3:14])[C:6](=[O:13])[NH:7]2.[CH2:15](I)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([O:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:14])[C:6](=[O:13])[NH:7]2)[CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 233696243,8-Dimethyl-5-hydroxycarbostyril

Product 1

HCID 233695515-Allyloxy-3,8-dimethylcarbostyrilYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5-Hydroxy-3,8-dimethylcarbostyril (4 g, 21.16 mmol) and allyl iodide (3.73 g, 22.2 mmol) were dissolved in dimethylformamide (44 ml), to which potassium carbonate (6.1 g, 44.2 mmol) was added, and stirred for 2 hours in a bath at 70° C. The solvent was distilled off, and the residue was dissolved in chloroform, and washed with water. After drying and condensing, the resultant residue was purified by silica gel chromatography (chloroform), and was subjected to recrystallization (chloroform-n-hexane) to obtain 4.32 g of the title compound as pale yellow prisms (89.2%).

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with water
  5. customAfter drying
  6. customcondensing
  7. customthe resultant residue was purified by silica gel chromatography (chloroform)
  8. customwas subjected to recrystallization (chloroform-n-hexane)

Sources & evidence

ORD record
ord-fc2d23a0f92643dc96bfca53f297a996
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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