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

Participants

Reaction Conditions

Reaction Steps

In 100 ml of toluene, 10.0 g (0.106 mol) of 2-aminopyridine was dissolved. After the solution was cooled to 5° C., 11.8 ml (0.159 mol) of trifluoroacetic acid and 9.9 ml (0.106 mol) of phosphorus oxychloride were added, followed by stirring at room temperature overnight. Then, 20 ml of toluene was distilled off under reduced pressure. To the reaction liquid, 50 ml of dimethylformamide, 35.28 g (0.256 mol) of potassium carbonate powder, and 17.22 g (0.106 mol) of 2-chloro-5-chloromethylpyridine were added under ice-cooling. Then, distillation was conducted under reduced pressure (60 to 35 hPa) at 50 to 60° C. Two hours later, 25 ml of dimethylformamide, 20 ml of toluene, and 7.35 g (0.053 mol) of potassium carbonate powder were further added, and then distillation was conducted under reduced pressure (60 to 35 hPa) at 50 to 60° C. for 2 hours. To the reaction liquid, 60 ml of methanol and 50 ml of water were added, and the reaction liquid was added to 300 ml of water, while the vessel was also washed. Thirty minutes later, the crystals were filtered, and washed with 70 ml of water and 40 ml of toluene. The obtained crystals were dried under reduced pressure at 60° C. Thus, 25.75 g of the target compound was obtained (76.9%).

Provenance & Evidence