2-Bromopyridine → 4-cyano-2-nitro-N-(2-pyridyl)aniline

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A mixture of 4-Cyano-2-nitroaniline (10.8 g, 66 mmol), 2-bromopyridine (12.6 g, 80 mmol), anhydrous potassium carbonate (9.12 g, 66 mmol) and copper-bronze (1.0 g, 15.7 mmol) in nitrobenzene (100 ml) was heated overnight at 200° C. The reaction mixture was cooled and filtered through a pad of celite. The filter cake was washed with dichloromethane (500 ml) and the filtrate was evaporated. The resultant residue was purified by column chromatography (silica gel, 500 g; n-hexane/ethyl acetate/dichloromethane (4/1/1)) to afford 7.28 g (46%) of 4-Cyano-2-nitro-N-(2-pyridyl)aniline as orange solids. 1H-NMR (CDCl3) δ: 10.53 (1H, br.s), 9.08 (1H, d, J=8.8 Hz), 8.58 (1H, d, J=8.8 Hz), 8.41 (1H, ddd, J=5.8, 1.8, 0.7 Hz), 7.78-7.69 (2H, m), 7.12-7.06 (1H, m), 7.02 (1H, d, J=8.8 Hz).

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