Acetylacetone → HCID 10966959, compound

HRID 1700513Notes

Reaction equation

HRID 1700513 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:19].[C:20]([CH2:23][C:24](=O)[CH3:25])(=O)[CH3:21]>C(O)C>[CH3:21][C:20]1[CH:23]=[C:24]([CH3:25])[C:10]2[C:9](=[O:14])[CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][C:11]=2[N:19]=1

Participants

5

Reactant 3

HCID 31261AcetylacetoneHCID 517165Ammonium AcetateHCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 10966959HCID 10966959, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 5-phenylcyclohexane-1,3-dione (2.0 g) and ammonium acetate (0.90 g) in ethanol (30 ml) was added acetylacetone (1.1 g), and the mixture was stirred at room temperature for 1 hour and refluxed for 21 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 insoluble materials were filtered off. The filtrate was concentrated, and the residue was purified with silica gel column chromatography (EtOAc/hexane). The resulting crystals were recrystallized from diisopropylether and hexane to give colorless crystals of 2,4-dimethyl-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one (0.6 g).

Workup

  1. temperaturerefluxed for 21 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure, and insoluble materials
  7. filtrationwere filtered off
  8. concentrationThe filtrate was concentrated
  9. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  10. customThe resulting crystals were recrystallized from diisopropylether and hexane

Sources & evidence

ORD record
ord-efbfdc3d1e40457c8c8cf97d966667b3
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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