Acetic Acid → 4-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-one

HRID 1839609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839609
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)=[CH:5][CH:4]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=[O:41])C>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][C:12](=[O:41])[NH:13]3)=[CH:7][CH:8]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 21124087PyridiniumtribromideHCID 225619404-(4-Methoxyphenyl)-1H-indole

Produkt 1

HCID 225619014-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-oneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 86587657t-BuOH ethanol aceticacidLösungsmittel

Reaktionsbedingungen

Temperatur
27 °C

Versuchsvorschrift

To the suspension of 4-(4-methoxy-phenyl)-1H-indole (1.84 g, 8.24 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (99 mL) was added pyridinium tribromide (90% purity from Aldrich, 8.78 g, 24.72 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (40 mL). Zinc dust was added to the reaction mixture portionwise until the color changed from deep red to light yellow, and the reaction mixture was stirred at room temperature for one hour. The unreacted zinc dust was filtered off and washed with ethanol. The filtrate was concentrated, and the syrupy residue was dissolved in ethyl acetate, which was washed with water, 0.5 N HCl, sat. NaHCO3 and brine, and dried over Na2SO4. After filtration and evaporation, the crude product was triturated with diethyl ether to provide product 4-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one (1.66 g, 84%) as a tan solid.

Aufarbeitung

  1. stirringwas stirred at room temperature for one hour
  2. filtrationThe unreacted zinc dust was filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe syrupy residue was dissolved in ethyl acetate
  6. washwhich was washed with water, 0.5 N HCl, sat. NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration and evaporation
  9. customthe crude product was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7e8568e468634bcfb7e6ed7ea077f7ad
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677368B2

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