Potassium Hydroxide → 7-(2-Fluoro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700697
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[F:15])[CH2:5][C:4](=[O:16])[CH:3]=1.[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[F:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[N:1]=[CH:7][CH:2]=[C:3]([CH3:4])[C:3]=2[C:4](=[O:16])[CH2:5]1

Komponenten

5

Edukt 2

HCID 14797Potassium Hydroxide4×HCID 183176231-Amino-5-(2-fluoro-5-methylphenyl)cyclohexen-3-one

Produkt 1

HCID 183175417-(2-Fluoro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneAusbeute 162,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In ethanol (35 ml) and toluene (60 ml) was dissolved 1-amino-5-(2-fluoro-5-methylphenyl)cyclohexen-3-one (1.3 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (2.0 g) and powdery potassium hydroxide (0.32 g). The mixture was refluxed, and to the mixture was added powdery potassium hydroxide (0.07 g), 30 minutes later; were added powdery potassium hydroxide (0.07 g) and 3-oxobutylaldehydedimethylacetal (0.16 g), 1 hour later; and was added powdery potassium hydroxide (0.07 g), 1.5 hours later. The mixture was stirred at the same temperature for 2 hours and cooled. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, ethyl acetate was evaporated, and the residue was purified with silica gel column (ethyl acetate-hexane). The resulting crystals were recrystallized from ethyl acetate-hexane to give 7-(2-fluoro-5-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.3 g).

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. temperaturecooled
  3. customUnder reduced pressure, the 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. customUnder reduced pressure, ethyl acetate was evaporated
  8. customthe residue was purified with silica gel column (ethyl acetate-hexane)
  9. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f690bbdecb884395aa396e160421c467
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350749B1

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