5-Nitro-2-phenyl-1H-indole → 2-phenyl-1H-indol-5-amine

HRID 1403907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1403907
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:7]2)([O-])=O>CO.[Ni]>[C:13]1([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 1

HCID 2803095-Nitro-2-phenyl-1H-indole

Produkt 1

HCID 98371822-phenyl-1H-indol-5-amineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77%). 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H+) 209.0.

Aufarbeitung

  1. filtrationThe catalyst was filtered through a Celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customto give the crude product, which
  4. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-84b152951dbd41d1b860abb1f13c42d4
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912199B2

Notizen zur Reaktion

Wird geladen…