2-Fluoropyridine → 2-Nitro-N-(2-pyridyl)-4-trifluoromethylaniline

Participants

Reaction Steps

To a stirred suspension of sodium hydride (2.40 g, 60 mmol) in dimethylacetamide (60 ml) at room temperature under a nitrogen atmosphere was added a solution of 2-nitro-4-trifluoromethylaniline (10.31 g, 50 mmol) in dimethylacetamide (20 ml) during 30 min. After stirring the mixture at room temperature for 15 min., a solution of 2-fluoropyridine (5.83 g, 60 mmol) in dimethylacetamide (20 ml) was added during 5 min. The resulting mixture was heated to reflux for about 8 h. Volatiles were removed by evaporation under reduced pressure. The residue was dissolved into ethyl acetate (200 ml) and washed with water (3×100 ml). The organic layer was dried (magnesium sulfate) and concentrated to dryness. Column chromatography (silica gel, 250 g; n-hexane/ethyl acetate (17/3)) yielded 3.38 g (23%) of the titled compound as yellow solids. 1 H-NMR (CDCl3) δ: 10.41 (1H, br.s), 9.02 (1H, d, J=9.2 Hz), 8.55-8.52 (1H, m), 8.42-8.38 (1H, m), 7.79-7.65 (2H, m), 7.05 (1H, dd, J=6.6, 4.8 Hz), 7.00 (1H, d, J=9.2 Hz).

Provenance & Evidence