反応 #79194

反応方程式

sodium hydride

2-fluoropyridine

2-nitro-4-trifluoromethylaniline

→

titled compound

収率 23.9%

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

収率 23.9%

溶媒

dimethylacetamide

dimethylacetamide

dimethylacetamide

反応条件

後処理

1. 1
   温度The resulting mixture was heated
2. 2
   温度to reflux for about 8 h
3. 3
   その他Volatiles were removed by evaporation under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved into ethyl acetate (200 ml)
5. 5
   洗浄washed with water (3×100 ml)
6. 6
   乾燥The organic layer was dried (magnesium sulfate)
7. 7
   濃縮concentrated to dryness

実験手順

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).

出典