Water → 3,8-Dimethyl-5-(2-butenyloxy)carbostyril

HRID 1900827Notes

Reaction equation

HRID 1900827 reaction equation
[CH3:1][C:2]1[C:3](=[O:14])[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][C:6]=2[CH3:13].[CH2:15](Br)[CH:16]=[CH:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][C:2]1[C:3](=[O:14])[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH2:15][CH:16]=[CH:17][CH3:18])[CH:8]=[CH:7][C:6]=2[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 233696243,8-Dimethyl-5-hydroxycarbostyril

Product 1

HCID 545443253,8-Dimethyl-5-(2-butenyloxy)carbostyrilYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3,8-Dimethyl-5-hydroxycarbostyril (3 g, 15.86 mmol) was dissolved in dimethylformamide (30 ml). To the solution, crotyl bromide (2.06 ml, 20.45 mmol) and potassium carbonate (4.4g, 31.84 mmol) were added. The mixture was stirred at 70° C. for 2 hours. After spontaneous cooling, water (90 ml) was added to the mixture. Precipitated crystals were collected by filtration. The obtained crystals were dissolved in chloroform, washed with water and saturated aqueous NaCl solution in this order, and dried. The solvent was distilled off under reduced pressure, and the residue was recrystallized from chloroform-n-hexane. As a result, 2.43 g of the title compound was obtained as colorless crystals (63%).

Workup

  1. customPrecipitated crystals
  2. filtrationwere collected by filtration
  3. dissolutionThe obtained crystals were dissolved in chloroform
  4. washwashed with water and saturated aqueous NaCl solution in this order
  5. customdried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was recrystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-53f1a79e0f474c6291c5c4afa2991c7f
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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