Ethyl propiolate → 7-Phenyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

HRID 1700520Notes

Reaction equation

HRID 1700520 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:19].[C:20]([O:24]CC)(=O)[C:21]#[CH:22]>C(O)C>[C:1]1([CH:7]2[CH2:8][C:9]3[NH:19][C:20](=[O:24])[CH:21]=[CH:22][C:10]=3[C:11](=[O:13])[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 12182Ethyl propiolateHCID 517165Ammonium AcetateHCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 135724197-Phenyl-7,8-dihydroquinoline-2,5(1H,6H)-dioneYield 14.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-phenylcyclohexane-1,3-dione (1.0 g) and ammonium acetate (0.45 g) in ethanol (30 ml) was stirred at room temperature for 1 hour, refluxed for 6 hours and cooled. To the reaction solution was added ethyl propiolate (0.55 g), and the mixture was stirred at room temperature for 1 hour and refluxed 14.5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was recrystallized from ethanol to give colorless crystals of 7-phenyl-1,2,5,6,7,8-hexahydroquinoline-2,5-dione (0.19 g).

Workup

  1. temperaturerefluxed for 6 hours
  2. temperaturecooled
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. temperaturerefluxed 14.5 hours
  5. customUnder reduced pressure, the solvent was evaporated
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-155396cd231943db9589db48f38dddf3
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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