Allyl iodide → HCID 23369583, compound

HRID 1900711Notes

Reaction equation

HRID 1900711 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[CH2:14](I)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:16]([O:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 23369598HCID 23369598, compound

Product 1

HCID 23369583HCID 23369583, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5-Hydroxy-8-methylcarbostyril (6.35 g, 36.3 mmol), allyl iodide (6.07 g, 36.1 mmol), n-tetrabutylammonium bromide (1.16 g, 36.1 mmol) were dissolved in dimethylformamide (108 ml). To the solution, potassium carbonate (10 g, 72.5 mmol) was added, and stirred in a bath of 50° C. for 2 hours. The solvent was evaporated, and the residue, dissolved in chloroform, was washed with water. The washed material was dried and condensed. The resultant residue was purified by silica gel column chromatography (eluent; chloroform). Recrystallization (chloroform-n-hexane) yielded 4.98 g of 5-allyloxy-8-methylcarbostyril as colorless flakes (63.8%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue, dissolved in chloroform
  3. washwas washed with water
  4. customThe washed material was dried
  5. customcondensed
  6. customThe resultant residue was purified by silica gel column chromatography (eluent; chloroform)
  7. customRecrystallization (chloroform-n-hexane)

Sources & evidence

ORD record
ord-b49c8ede6e344a4d980ee7ec72cd537e
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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