Ethanol → HCID 18317361, compound

HRID 1700499Notes

Reaction equation

HRID 1700499 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:12][C:11](=[O:13])[CH2:10][C:9](=O)[CH2:8]1.[C:15]([O-])(=O)[CH3:16].[NH4+:19].[CH2:20](O)[CH3:21]>>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:8][C:9]2[N:19]=[CH:20][CH:21]=[C:15]([CH3:16])[C:10]=2[C:11](=[O:13])[CH2:12]1

Participants

4

Reactant 3

HCID 702EthanolHCID 517165Ammonium AcetateHCID 18317511HCID 18317511, compound

Product 1

HCID 18317361HCID 18317361, compound

Procedure

A solution of 5-(3-chloro-2-thienyl)-1,3-cyclohexanedione (0.6 g) and ammonium acetate (0.61 g) in ethanol (20 ml) was refluxed for 13 hours. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate and water. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethanol (6 ml) and toluene (18 ml). To the solution were added acetylacetoaldehydedimethylacetal (0.86 g) and powdery 85% potassium hydroxide (0.14 g), and the mixture was refluxed. With 30 minutes interval, powdery 85% potassium hydroxide (0.029 g) was added thrice to the mixture, and the mixture was refluxed for 1 hour. 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) to give oil of crude 7-(3-chloro-2-thienyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.3 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue were added ethyl acetate and water
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethanol (6 ml)
  7. additionTo the solution were added acetylacetoaldehydedimethylacetal (0.86 g) and powdery 85% potassium hydroxide (0.14 g)
  8. temperaturethe mixture was refluxed
  9. additionWith 30 minutes interval, powdery 85% potassium hydroxide (0.029 g) was added thrice to the mixture
  10. temperaturethe mixture was refluxed for 1 hour
  11. customUnder reduced pressure, the solvent was evaporated
  12. additionto the residue was added ethyl acetate
  13. washThe mixture was washed with water and saturated brine
  14. dry with materialdried with magnesium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-9b098c91222a462c91697b314a231b3f
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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