Reaktion #594700

Reaktionsgleichung

5-nitrobenzo[b]thiophene

→

benzo[b]thiophen-5-amine

Ausbeute 101.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter 16 h the catalyst was filtered off over a celite pad
2. 2
   Waschenwashed with ethanol (2×30 mL)
3. 3
   SonstigeThe filtrate was evaporated in vacuo

Vorschrift

A mixture of 5-nitrobenzo[b]thiophene (3.09 g, 17.0 mmol) and 10% palladium on carbon (Aldrich, cat. No. 20,569-9) (150 mg) in ethanol (90 mL) was shaken in a Parr flask under a hydrogen atmosphere of 3 bar. After 16 h the catalyst was filtered off over a celite pad and washed with ethanol (2×30 mL). The filtrate was evaporated in vacuo to yield benzo[b]thiophen-5-amine (2.57 g, 100%) as a dark purple amorphous solid. 1H NMR δ (CDCl3, 400 MHz) 3.70 (br. s., 2H), 6.78 (dd, J=8.61, 1.96 Hz, 1H), 7.10 (d, J=2.35 Hz, 1H), 7.14 (d, J=5.09 Hz, 1H), 7.38 (d, J=5.48 Hz, 1H), 7.63 (d, J=8.61 Hz, 1H)

Quelle