5-tert-butyl-6-nitro-1H-indole → HCID 57470208, Verbindung

HRID 469991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469991
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH2:14])[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 574702075-tert-butyl-6-nitro-1H-indole

Produkt 1

HCID 57470208HCID 57470208, VerbindungAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Raney Ni (3 g) was added to 5-tert-butyl-6-nitro-1H-indole (14.7 g, 67 mmol) in methanol (100 mL). The mixture was stirred under hydrogen (1 atm) at 30° C. for 3 h. The catalyst was filtered off. The filtrate was dried over Na2SO4 and concentrated. The crude dark brown viscous oil was purified by column chromatography (10-20% EtOAc/petroleum ether) to give 5-tert-butyl-1H-indol-6-ylamine (B-24) as a gray solid (11 g, 87%). 1H NMR (300 MHz, DMSO-d6) δ 10.3 (br s, 1H), 7.2 (s, 1H), 6.9 (m, 1H), 6.6 (s, 1H), 6.1 (m, 1H), 4.4 (br s, 2H), 1.3 (s, 9H).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. dry with materialThe filtrate was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude dark brown viscous oil was purified by column chromatography (10-20% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-85daf76acd03409aad2b174a03a7f654
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629162B2

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