反应详情

Under an atmosphere of nitrogen, a mixture of 38.5 g (250 mmol) of ethyl 6-methylnicotinate, 29.9 g (500 mmol) of sodium methoxide (90.5%) and 300 ml of toluene was added, at 85-90° C. and over the course of 30 min, to a solution of 47.3 g (250 mmol) of 4-(methylthio)phenylacetonitrile in 75 ml of toluene. This mixture was stirred under reflux for 14 h, then distilled until the overhead temperature exceeded 110° C. and kept at reflux for another 6 h. The reaction mixture was poured into 500 g of ice water, the organic phase was decanted off and the aqueous phase was extracted with 3×100 ml of toluene. The aqueous phase was acidified to pH 6.0 using conc. HCl. The resulting yellow-beige suspension was filtered and the residue was washed with water and dried. This gave 53.9 g (76%) of the title product in the form of a yellow solid.

1. temperatureunder reflux for 14 h
2. distillationdistilled until the overhead temperature
3. customexceeded 110° C.
4. temperatureat reflux for another 6 h
5. additionThe reaction mixture was poured into 500 g of ice water
6. customthe organic phase was decanted off
7. extractionthe aqueous phase was extracted with 3×100 ml of toluene
8. filtrationThe resulting yellow-beige suspension was filtered
9. washthe residue was washed with water
10. customdried