Pyridine → 1H-Indole-6-carboxaldehyde

HRID 351595

Reaktionsgleichung

Reaktionsgleichung von HRID 351595
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1)#N.[PH2]([O-])=[O:13].[Na+].N1C=CC=CC=1>O.C(O)(=O)C.[Ni]>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([CH:1]=[O:13])[CH:11]=2)[CH:7]=[CH:8]1

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 851461H-indole-6-carbonitrileHCID 178527019HCID 178527019, Verbindung

Produkt 1

HCID 27734351H-Indole-6-carboxaldehydeAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of 6-cyanoindole (15.0 g) and sodium hypophosphite (90 g) in water (326 mL), acetic acid (326 mL), and pyridine (652 mL) was added Raney Nickel catalyst and the mixture stirred at 45° C. for 45 minutes. The mixture was filtered through Celite and the filtrate extracted with ethyl acetate (3×500 mL). The extracts were dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was crystallized from a mixture of dichloromethane and hexanes to provide 13.6 g (89%) of the title compound.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. extractionthe filtrate extracted with ethyl acetate (3×500 mL)
  3. dry with materialThe extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was crystallized from a mixture of dichloromethane and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5f783d89b2e94c15bce37332941c245c
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743785B2

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