Potassium Hydroxide → HCID 18317328, compound

HRID 1700498Notes

Reaction equation

HRID 1700498 reaction equation
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[CH3:13])[CH2:5][C:4](=[O:14])[CH:3]=1.[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[CH3:4][C:3]1[C:3]2[C:4](=[O:14])[CH2:5][CH:6]([C:8]3[S:9][CH:10]=[CH:11][C:12]=3[CH3:13])[CH2:7][C:2]=2[N:1]=[CH:7][CH:2]=1

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 18317628HCID 18317628, compound

Product 1

HCID 18317328HCID 18317328, compoundYield 137.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-amino-5-(3-methyl-2-thienyl)cyclohexen-3-one (2.7 g) in ethanol (50 ml) and toluene (150 ml) were added acetylacetoaldehydedimethylacetal (4.3 g) and 85% potassium hydroxide (0.71 g), and the mixture was refluxed. With 30 minutes interval, 85% potassium hydroxide (0.15 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 crystals of 4-methyl-7-(3-methyl-2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (2.3 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturethe mixture was refluxed for 1 hour
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionto the residue was added ethyl acetate
  5. washThe mixture was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-1fce51849eca434e9db675b4bc674901
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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