[2-(5-Fluoro-2,4-dinitro-phenyl)-vinyl]-dimethyl-amine → 5-Fluoro-1H-indol-6-amine

HRID 1529641

Reaktionsgleichung

Reaktionsgleichung von HRID 1529641
[F:1][C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]([N+:13]([O-])=O)=[C:6]([CH:8]=[CH:9]N(C)C)[CH:7]=1>CCO.[Ni]>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[NH2:16])[NH:13][CH:9]=[CH:8]2

Komponenten

4

Edukt 1

HCID 57060726[2-(5-Fluoro-2,4-dinitro-phenyl)-vinyl]-dimethyl-amine

Produkt 1

HCID 150223365-Fluoro-1H-indol-6-amineAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of [2-(5-fluoro-2,4-dinitro-phenyl)-vinyl]-dimethyl-amine (8 g, 31.4 mmol) and Raney Ni (8 g) in EtOH (80 mL) was stirred under H2 (40 psi) at room temperature for 1 h. After filtration, the filtrate was concentrated and the residue was purified by chromatography (Pet.Ether/EtOAc=5/1) to give 5-fluoro-1H-indol-6-ylamine (B-20) as a brown solid (1 g, 16%). 1H NMR (DMSO-d6) δ 10.56 (br s, 1H), 7.07 (d, J=12 Hz, 1H), 7.02 (m, 1H), 6.71 (d, J=8 Hz, 1H), 6.17 (s, 1H), 3.91 (br s, 2H); ESI-MS 150.1 m/z (MH+).

Aufarbeitung

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by chromatography (Pet.Ether/EtOAc=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-e18aa802e8724a04a725a55737cf8696
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090619B2

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