反应详情

温度

97.5 °C

132 g of phosphoryl chloride are added, at 25° C., to 50 g of diethyl 2-[(4-methoxyphenylamino)methylene]malonate. The reaction medium is stirred for 15 minutes at this temperature, heated to 95-100° C. over 45 minutes, and then kept at this temperature for 4 hours. The excess phosphoryl chloride is then removed by heating at 125° C. for approximately 2 hours. The mixture is then cooled to 25° C. and 125 ml of dichloromethane are added. The medium is then stirred at 25° C. for 1 hour, and then run into 900 ml of water, over 30 minutes, while maintaining the temperature below 30° C. The pH is then adjusted to 7.5-8 by adding 172 g of a 47% sodium hydroxide solution, while maintaining the temperature at 20-25° C. The 2 phases are separated and the aqueous phase is extracted with dichloromethane. The organic phases are pooled and washed with water. The dichloromethane phase is half-concentrated and 190 ml of ethanol are added. The concentration is continued until the temperature of the reaction mass reaches 82° C. and the vapor temperature reaches 78° C. The reaction mass is cooled to 0-5° C. and then kept at this temperature for 2 hours. The precipitate is filtered off, washed with cold ethanol, and then dried at 50° C. under reduced pressure. 27.7 g (61%) of 4-chloro-3-ethoxycarbonyl-6-methoxyquinoline are obtained in the form of a yellow solid which melts at 93.7-95.7° C.

1. waitkept at this temperature for 4 hours
2. customThe excess phosphoryl chloride is then removed
3. temperatureby heating at 125° C. for approximately 2 hours
4. temperatureThe mixture is then cooled to 25° C.
5. addition125 ml of dichloromethane are added
6. stirringThe medium is then stirred at 25° C. for 1 hour
7. waitrun into 900 ml of water, over 30 minutes
8. temperaturewhile maintaining the temperature below 30° C
9. additionby adding 172 g of a 47% sodium hydroxide solution
10. temperaturewhile maintaining the temperature at 20-25° C
11. customThe 2 phases are separated
12. extractionthe aqueous phase is extracted with dichloromethane
13. washwashed with water
14. concentrationThe dichloromethane phase is half-concentrated
15. addition190 ml of ethanol are added
16. concentrationThe concentration
17. customreaches 82° C.
18. customreaches 78° C
19. temperatureThe reaction mass is cooled to 0-5° C.
20. waitkept at this temperature for 2 hours
21. filtrationThe precipitate is filtered off
22. washwashed with cold ethanol
23. customdried at 50° C. under reduced pressure