Ethanol → HCID 18317582, compound

HRID 1700629Notes

Reaction equation

HRID 1700629 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][C:10](=[O:12])[CH2:9][C:8](=O)[CH2:7]1.[C:14]([O-])(=O)[CH3:15].[NH4+:18].[OH-].[K+].[CH2:21](O)[CH3:22]>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:7][C:8]2[N:18]=[CH:21][CH:22]=[C:14]([CH3:15])[C:9]=2[C:10](=[O:12])[CH2:11]1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 14797Potassium Hydroxide4×HCID 517165Ammonium AcetateHCID 18317567HCID 18317567, compound

Product 1

HCID 18317582HCID 18317582, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(2-thiazolyl)-cyclohexane-1,3-dione (0.93 g) and ammonium acetate (1.1 g) in ethanol (20 ml) was refluxed for 13 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution. The aqueous layer was washed with ethyl acetate and concentrated, and to the residue was ethanol-ethyl acetate (1:1). Insoluble materials were filtered and concentrated under reduced pressure. To the residue was added ethanol, and insoluble materials were filtered and concentrated under reduced pressure to give solid, which was dissolved in ethanol (10 ml) and toluene (30 ml). To the solution were added 3-oxobutylaldehydedimethylacetal (1.6 g) and powdery 85% potassium hydroxide (0.26 g), and the mixture was refluxed. To the mixture was added powdery 85% potassium hydroxide (0.054 g), 30 minutes later; were added powdery 85% potassium hydroxide (0.054 g) and 3-oxobutylaldehydedimethylacetal(0.063 g), 1 hour later; and powdery 85% potassium hydroxide (0.054 g), 1.5 hours later; and then the mixture was refluxed for 1 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) to give crystals of 7-(2-thiazolyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.76 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. additionto the residue was added sodium hydrogen carbonate solution
  3. washThe aqueous layer was washed with ethyl acetate
  4. concentrationconcentrated
  5. filtrationInsoluble materials were filtered
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added ethanol, and insoluble materials
  8. filtrationwere filtered
  9. concentrationconcentrated under reduced pressure
  10. customto give solid, which
  11. temperaturethe mixture was refluxed
  12. temperatureand then the mixture was refluxed for 1 hours
  13. customUnder reduced pressure, the solvent was evaporated
  14. additionto the residue was added ethyl acetate
  15. washThe mixture was washed with water and saturated brine
  16. dry with materialdried with magnesium sulfate
  17. concentrationconcentrated under reduced pressure
  18. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-2f198ac13bd64b9182348f28cea6b9bb
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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