3-methyl-6-nitro-1H-indole → 3-Methyl-1h-indol-6-amine

HRID 73923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73923
CC1C2C(=CC=CC=2[N+]([O-])=O)NC=1.[CH3:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([N+:24]([O-])=O)=[CH:21][CH:22]=2)[NH:17][CH:16]=1>C(O)C.[Pd]>[CH3:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([NH2:24])=[CH:21][CH:22]=2)[NH:17][CH:16]=1

Komponenten

5

Edukt 2

HCID 33588543-methyl-6-nitro-1H-indoleHCID 38071223-methyl-4-nitro-1H-indole

Produkt 1

HCID 189160403-Methyl-1h-indol-6-amineAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-methyl-4-nitro-1H-indole and 3-methyl-6-nitro-1H-indole (3 g, 17 mol) and 10% Pd—C (0.5 g) in ethanol (30 mL) was stirred overnight under H2 (1 atm) at room temperature. Pd—C was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to give 3-methyl-1H-indol-6-ylamine (B-7) (0.6 g, 24%). 1H NMR (CDCl3) δ 7.59 (br s, 1H), 7.34 (d, J=8.0 Hz, 1H), 6.77 (s, 1H), 6.64 (s, 1H), 6.57 (m, 1H), 3.57 (br s, 2H), 2.28 (s, 3H); ESI-MS 147.2 m/z (MH+).

Aufarbeitung

  1. filtrationPd—C was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9f54cbe322a842e2ab7390df5ea71026
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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