5-Nitro-1-benzothiophene → Benzo(b)thiophen-5-amine

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Reaction Steps

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., 2 H), 6.78 (dd, J=8.61, 1.96 Hz, 1 H), 7.10 (d, J=2.35 Hz, 1 H), 7.14 (d, J=5.09 Hz, 1 H), 7.38 (d, J=5.48 Hz, 1 H), 7.63 (d, J=8.61 Hz, 1 H).

Provenance & Evidence