Potassium Carbonate → HCID 54330815, compound

HRID 1900837Notes

Reaction equation

HRID 1900837 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:15])([CH3:14])[C:6](=[O:13])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH:24][CH3:25]>CN(C)C=O>[CH2:22]([O:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:15])([CH3:14])[C:6](=[O:13])[NH:7]2)[CH:23]=[CH:24][CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 23369635HCID 23369635, compound

Product 1

HCID 54330815HCID 54330815, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-hydroxy-3,3,8-trimethyl-3,4-dihydrocarbostyril (23 g, 11.2 mmol) and potassium carbonate (3.1 g, 22.4 mmol) in dimethylformamide (20 ml), crotyl bromide (1.8 g, 13.4 mmol) was added and stirred at 70° C. for 2 hours. The reaction mixture was poured into ice-water, and precipitated crystals were collected by filtration. The collected crude crystals were dissolved in chloroform, washed with water, and dried. The solvent was evaporated, and the residue was recrystallized from chloroform-hexane. 1.9 g of the title compound was obtained as colorless needles (65.4%).

Workup

  1. customprecipitated crystals
  2. filtrationwere collected by filtration
  3. customThe collected crude crystals
  4. dissolutionwere dissolved in chloroform
  5. washwashed with water
  6. customdried
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-339b52a6b59b48c5a5571dd6c56722a2
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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