6-Chloroindoline-2,3-dione → 5-Amino-6-chloroindole-3-acetonitrile

HRID 1381557

Reaktionsgleichung

Reaktionsgleichung von HRID 1381557
ClC1C=C2C(C(=O)C(=O)N2)=CC=1.ClC1C=C2C(C(=O)C(=O)N2)=CC=1[N+]([O-])=O.ClC1C=C2C(C=CN2)=CC=1[N+]([O-])=O.[Cl:41][C:42]1[CH:50]=[C:49]2[C:45]([C:46]([CH2:51][C:52]#[N:53])=[CH:47][NH:48]2)=[CH:44][C:43]=1[N+:54]([O-])=O.[H][H]>[Pd].CCO>[NH2:54][C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][C:42]=1[Cl:41])[NH:48][CH:47]=[C:46]2[CH2:51][C:52]#[N:53]

Komponenten

8

Edukt 5

HCID 2413316-Chloroindoline-2,3-dioneHCID 189328576-chloro-5-nitro-1H-indoleHCID 212762006-Chloro-5-nitroindole-3-acetonitrileHCID 233544316-Chloro-5-nitroisatinHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 212761865-Amino-6-chloroindole-3-acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

This intermediate was prepared by the sequence 6-chloroisatin, 6-chloro-5-nitroisatin, 6-chloro-5-nitroindole, 6-chloro-5-nitrogramine and 6-chloro-5-nitroindole-3-acetonitrile which was hydrogenated with 10% Pd/C until 3 equiv. of hydrogen were taken up. The catalyst was removed by filtration and the residue concentrated in vacuo to give a dark brown solid. Trituration with cold EtOH gave desired pure product.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationthe residue concentrated in vacuo
  3. customto give a dark brown solid

Quellen und Nachweise

ORD-Eintrag
ord-0a418df9f188460d8a5d72c1cd6bec41
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803218

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