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

HRID 469962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469962
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, 1 H), 7.34 (d, J=8.0 Hz, 1 H), 6.77 (s, 1H), 6.64 (s, 1 H), 6.57 (m, 1 H), 3.57 (br s, 2 H), 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-aa3e81a3b09f486ea0cdf9daeccc5312
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629162B2

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