Sodium Methoxide → 4-Methoxy-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700507Notes

Reaction equation

HRID 1700507 reaction equation
Cl[C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[CH3:19][O-:20].[Na+]>CO>[CH3:19][O:20][C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 183173374-Chloro-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one

Product 1

HCID 183177154-Methoxy-7-phenyl-5,6,7,8-tetrahydroquinolin-5-oneYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one (0.23 g) in methanol (20 ml) was added sodium methoxide (0.096 g), and the mixture was refluxed for 1 hour and cooled. The solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate-hexane to give crystals of 4-methoxy-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one (0.21 g).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. customThe solvent was evaporated
  4. additionto the residue was added ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e735799c434340bfb4ecce0de73dd741
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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