8-Chloro-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one → 2-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

HRID 1637259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637259
Cl[C:2]1[C:10]2[NH:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:7]3[CH2:17][CH2:18][C:19](=[O:20])[C:5]([C:6]=23)=[CH:4][CH:3]=1>[OH-].[K+].CO.[C].[Pd]>[C:11]1([C:8]2[NH:9][C:10]3[CH:2]=[CH:3][CH:4]=[C:5]4[C:19](=[O:20])[CH2:18][CH2:17][C:7]=2[C:6]=34)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 1

HCID 193481908-Chloro-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

Produkt 1

HCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-oneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

A portion (2.4 g) of the compound obtained in Example 60 was dissolved in a solution of potassium hydroxide (3 g) in methanol (150 ml) and to the solution was added 10% palladium-carbon (500 mg). The mixture was stirred for 30 minutes at room temperature under a hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10:1-2:1) to yield 700 mg (39%) of the titled compound.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-928e59bdd82b44ebaa064274670c3cd6
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040331

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