反应详情

To a solution of 2-chloro-4-phenylnicotinic acid (22.4 g) in tetrahydrofuran (200 ml) was added thionyl chloride (21 ml), and the mixture was heated under reflux for 3 hrs. The solvent was evaporated under reduced pressure, and the precipitated solid was collected by filtration and washed with hexane. The obtained powdery solid was dissolved in tetrahydrofuran (200 ml), and lithium aluminum hydride (4.5 g) was added by small portions while cooling in a dry ice-acetone bath. The mixture was stirred under cooling for 5 min. and water was added to quench the reaction. The precipitated solid was filtered off, and the filtrate was concentrated and extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (15.1 g) as a colorless oil.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 3 hrs
3. customThe solvent was evaporated under reduced pressure
4. filtrationthe precipitated solid was collected by filtration
5. washwashed with hexane
6. dissolutionThe obtained powdery solid was dissolved in tetrahydrofuran (200 ml)
7. additionlithium aluminum hydride (4.5 g) was added by small portions
8. temperaturewhile cooling in a dry ice-acetone bath
9. temperatureunder cooling for 5 min.
10. additionwater was added
11. customto quench
12. customthe reaction
13. filtrationThe precipitated solid was filtered off
14. concentrationthe filtrate was concentrated
15. extractionextracted with ethyl acetate
16. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated brine
17. dry with materialdried over anhydrous magnesium sulfate
18. customthe solvent was evaporated under reduced pressure