Trifluoroacetic acid → N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide

Participants

Reaction Conditions

Reaction Steps

In 40 ml of xylene, 2.35 g (0.025 mol) of 2-aminopyridine was suspended. To this mixture, 2.85 g (0.025 mmol) of trifluoroacetic acid and 135 mg of ferric chloride hexahydrate were added, and attached a Dean-Stark trap. The mixture was stirred at 150° C. for 16 hours, removing the resulting water by the Dean-Stark trap. After the solution was cooled to 60° C., 4.05 g (0.025 mol) of 2-chloro-5-chloromethylpyridine, 16 mL of dimethylformamide, and 2.42 g (0.0175 mol) of potassium carbonate were added, followed by stirring under a reduced pressure of 60-110 hPa at 60 to 65° C. for 3 hours. Then, 10 mL of methanol was added to the reaction mixture, and this mixture was added to 80 mL of hot water of 50° C. The mixture was cooled to room temperature with stirring. Crystals were filtered, and washed with 20 mL of water and 20 mL of toluene. The obtained crystals were dried under reduced pressure at 60° C. Thus, 6.32 g of the target compound was obtained (Percentage Yield: 80.3%).

Provenance & Evidence