(2-Nitropyridin-3-yl)phenylamine → N3-Phenylpyridine-2,3-diamine

Beteiligte Stoffe

Reaktionsschritte

A mixture of (2-nitropyridin-3-yl)phenylamine (6.75 mmol) in EtOAc (40 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (200 mg) and was stirred at RT under a hydrogen atmosphere for 16 h. The suspension was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford the title compound as a white solid (520 mg, 42% over two steps). 1H NMR (CDCl3, 400 MHz): δ 7.92 (1H, dd, J=4.98, 1.64 Hz), 7.36 (1H, ddd, J=7.62, 1.65, 0.69 Hz), 7.26-7.20 (2H, m), 6.90-6.85 (1H, m), 6.78-6.73 (2H, m), 6.68 (1H, dd, J=7.61, 4.98 Hz), 5.13 (1H, br s), 4.57 (2H, br s).

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