6-Nitro-1H-indole-3-carbonitrile → 6-amino-1H-indole-3-carbonitrile

HRID 468389

Reaktionsgleichung

Reaktionsgleichung von HRID 468389
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1

Komponenten

4

Edukt 1

HCID 2831796-Nitro-1H-indole-3-carbonitrile

Produkt 1

HCID 444104646-amino-1H-indole-3-carbonitrileAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 6-nitro-1H-indole-3-carbonitrile (4.6 g, 25 mmol) and 10% Pd—C (0.46 g) in EtOH (50 mL) was stirred under H2 (1 atm) at room temperature overnight. After filtration, the filtrate was concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=3/1) to give 6-amino-1H-indole-3-carbonitrile (1.0 g, 98%) as a pink solid, 1H NMR (DMSO-d6) δ 11.51 (s, 1H), 7.84 (d, J=2.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 6.62 (s, 1H), 6.56 (d, J=8.4 Hz, 1H), 5.0 (s, 2H); MS (ESI) m/e (M+H+) 157.1.

Aufarbeitung

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-548bf1649087497b9b978a55ae47a6df
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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