Reaktion #91520

Reaktionsgleichung

5-nitro-1H-indole

Pd/C

(4-Phenylpiperidin-1-yl)(3,4,5-trimethoxyphenyl)methanone

→

5-aminoindole

Ausbeute 92.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Sonstigethe excess of ethanol was evaporated under reduced pressure
3. 3
   SonstigeSolid product was recrystallized from hexane

Vorschrift

A mixture of 5-nitro-1H-indole (11 g, 67.9 mmol) and Pd/C (5%; 1g), dissolved in ethanol (50 mL), was hydrogenated for 3 h at 40 psi. The reaction mixture was filtered and the excess of ethanol was evaporated under reduced pressure. Solid product was recrystallized from hexane to obtain the pure compound 5-aminoindole (55-1). Yield: 92.5%. 1H NMR (500 MHz, CDCl3): δ 7.96 (br, 1H), 7.20 (d, 1H), 7.13 (s, 1H), 6.95 (s, 1H), 6.67 (dd, 1H), 6.37 (s, 1H), 3.50 (s, 2H). MS (ESI) m/z 133.0 (M+H)+

Quelle