反应详情

温度

200 °C

6.84 g (25 mmol) of 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyridine (content 99.5 percent prepared according to Example 1), 4.17 g (37.5 mmol) of 4-fluoroaniline, 2.92 g (27.5 mmol) of sodium carbonate, 0.27 g (0.25 mmol) of palladium/activated charcoal (10 percent Pd) and 0.32 g (0.75 mmol) of 1,4-bis(diphenylphosphino)butane (IV, n=4, R8=R9=R10=R11=phenyl) in 25 ml of xylene were placed in an autoclave at room temperature. The autoclave was flushed with inert gas, carbon monoxide was then introduced under a pressure of 5 bar and the temperature was raised to 200° C. The CO pressure was increased to 14.5 bar and the mixture was stirred for 16 hours at 200° C. After cooling to room temperature and depressurization, the reaction mixture was treated with 50 ml of xylene and 50 ml of water and filtered. The aqueous phase was extracted with 25 ml of xylene and the combined organic phases were washed with 30 ml of water. The composition of the dissolved products was determined by GC. 92.1 percent of the title compound (amide), 1.9 percent of educt and 6.0 percent of by-products (3.1 percent of secondary amine formed by direct substitution of Cl by the aniline, and 2.9 percent of 2-[3-(trifluoromethyl)phenoxy]pyridine formed by hydrogenolysis) were found. After distillation of the solvent, the crude product (8.63 g) was obtained in the form of a yellow solid. The crude product was purified by recrystallization from methylcyclohexane. the yield of the title compound product was 6.3 g (67 percent) of colorless crystals. The melting point of the product was 104° to 105° C. Other data concerning the title compound was:

1. customwere placed in an autoclave at room temperature
2. customThe autoclave was flushed with inert gas, carbon monoxide
3. additionwas then introduced under a pressure of 5 bar
4. temperatureThe CO pressure was increased to 14.5 bar
5. temperatureAfter cooling to room temperature
6. additiondepressurization, the reaction mixture was treated with 50 ml of xylene and 50 ml of water
7. filtrationfiltered
8. extractionThe aqueous phase was extracted with 25 ml of xylene
9. washthe combined organic phases were washed with 30 ml of water