HCID 59129336, Verbindung → 2-(1-methyl-cyclopropyl)-1H-indol-5-ylamine

HRID 1847429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1847429
[CH3:1][C:2]1([C:5]2[NH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][CH:8]=3)[CH2:4][CH2:3]1>CCO.[Ni]>[CH3:1][C:2]1([C:5]2[NH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([NH2:14])=[CH:9][CH:8]=3)[CH2:4][CH2:3]1

Komponenten

4

Edukt 1

HCID 59129336HCID 59129336, Verbindung

Produkt 1

HCID 591295412-(1-methyl-cyclopropyl)-1H-indol-5-ylamineAusbeute 28,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(1-methylcyclopropyl)-5-nitro-1H-indole (0.70 g, 3.2 mmol) in EtOH (20 mL) was added Raney Nickel (100 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to afford 2-(1-methyl-cyclopropyl)-1H-indol-5-ylamine (170 mg, 28%). 1H NMR (400 MHz, CDCl3) δ 7.65 (brs, 1H), 7.08 (d, J=8.4 Hz, 1H), 6.82 (s, 1H), 6.57 (d, J=8.4 Hz, 1H), 6.14 (s, 1H), 3.45 (brs, 2H), 1.47 (s, 3H), 0.82-0.78 (m, 2H), 0.68-0.63 (m, 2H).

Aufarbeitung

  1. filtrationThe catalyst was filtered off through a celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-5b23fbf46d4441bc81ffa7e0c108357b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952050B2

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