反应详情

温度

50 °C

A mixture of 118.6 parts of methyl 4-(acetylamino)-2-ethoxybenzoate, 200 parts of acetic acid and 156 parts of acetic acid anhydride was stirred and heated to 50° C. After cooling to 15° C. (ice-bath) there were added dropwise 47.1 parts of fuming nitric acid 100% using a bromine funnel: an exothermic reaction occured. The temperature was kept at about 20° C. by cooling in an ice-bath. Upon completion, the temperature was allowed to rise to 40° C. and stirring was continued at this temperature for one hour. If necessary the whole was cooled with ice-water to keep the temperature at about 40° C. When the exothermic reaction was ceased, the whole was allowed to cool for one hour and was further cooled to 0° C. The reaction mixture was poured onto icewater while stirring. Upon stirring for one hour, the precipitated product was filtered off and dissolved in 1950 parts of dichloromethane. The solution was washed twice with 500 parts of water, dried, filtered and evaporated. The residue was crystallized overnight at room temperature from 2-propanol. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 67.6 parts (47.9%) of methyl 4-(acetylamino)-2-ethoxy-5-nitrobenzoate; mp. 110° C. (intermediate 32).

1. temperatureAfter cooling to 15° C. (ice-bath) there
2. customan exothermic reaction
3. customwas kept at about 20° C.
4. temperatureby cooling in an ice-bath
5. customto rise to 40° C.
6. stirringstirring
7. customat about 40° C
8. customWhen the exothermic reaction
9. temperatureto cool for one hour
10. temperaturewas further cooled to 0° C
11. additionThe reaction mixture was poured onto icewater
12. stirringwhile stirring
13. stirringUpon stirring for one hour
14. filtrationthe precipitated product was filtered off
15. dissolutiondissolved in 1950 parts of dichloromethane
16. washThe solution was washed twice with 500 parts of water
17. customdried
18. filtrationfiltered
19. customevaporated
20. customThe residue was crystallized overnight at room temperature from 2-propanol
21. filtrationThe product was filtered off
22. washwashed with 2,2'-oxybispropane
23. customdried