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

HRID 1727492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727492
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, 1 h), 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-3c5f3cab068d4de0aeabd967f7ac4855
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495103B2

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