Ethanol → HCID 11822907, compound

HRID 1700632Notes

Reaction equation

HRID 1700632 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH2:12][C:11](=O)[CH2:10]1.[C:17]([O-])(=O)[CH3:18].[NH4+:21].[OH-].[K+].[CH2:24](O)[CH3:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:10][C:11]2[N:21]=[CH:24][CH:25]=[C:17]([CH3:18])[C:12]=2[C:13](=[O:15])[CH2:14]1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 14797Potassium Hydroxide4×HCID 517165Ammonium AcetateHCID 18317327HCID 18317327, compound

Product 1

HCID 11822907HCID 11822907, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(2,5-dichlorophenyl)-cyclohexane-1,3-dione (5.0 g) and ammonium acetate (4.5 g) in ethanol (100 ml) was refluxed for 20.5 hours. Under reduced pressure, the solvent was evaporated, and the residue was washed with water and toluene and dried to give crystals, which were dissolved in ethanol (50 ml) and toluene (150 ml). To the solution were added 3-oxobutylaldehydedimethylacetal (6.1 g) and powdery 85% potassium hydroxide (1.0 g), and the mixture was refluxed. To the mixture was added powdery 85% potassium hydroxide (0.21 g), 30 minutes later; were added powdery 85% potassium hydroxide (0.21 g) and 3-oxobutylaldehydedimethylacetal(0.24 g), 1 hour later; and powdery 85% potassium hydroxide (0.21 g), 1.5 hours later; and then the mixture was refluxed for 1.5 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The mixture was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane). The resulting crystals were recrystallized from ethyl acetate-hexane to give 7-(2,5-dichlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (3.7 g) as crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. washthe residue was washed with water and toluene
  3. customdried
  4. customto give crystals, which
  5. temperaturethe mixture was refluxed
  6. temperatureand then the mixture was refluxed for 1.5 hours
  7. customUnder reduced pressure, the solvent was evaporated
  8. additionto the residue was added ethyl acetate
  9. washThe mixture was washed with water and saturated brine
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  13. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-555037d3a9914ed1aee93215ef689a3d
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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