反应详情

温度

37.5 °C

Magnesium (2.08 g), toluene (40 ml), triethylamine (10.4 g) were put into a 3″ diameter flask, and the internal temperature was raised to 30 to 45° C. A solution of 1-iodebutane (18.9 g) in toluene was added under stirring at an internal temperature of 30 to 45° C. After stirring for two hours at the same temperature, the temperature was lowered to 0 to 5° C., thereby preparing a solution of iode n-butylmagnesium in toluene. To this prepared Grignard reagent, indole (10.0 g) dissolved beforehand in toluene (25 ml) was added at an internal temperature of 0 to 10° C., and a reaction was carried out for about one hour at the same temperature to synthesize iodeindole-1-ylmagnesium. Then, m-nitrobenzoyl chloride (15.8 g) and toluene (60 ml) were put into another 3″ diameter flask, and the internal temperature was lowered to below −15° C. The slurry of the iodeindole-1-ylmagnesium prepared previously was added to the solution of this acid chloride while keeping the internal temperature at −15 to −10° C., and the mixture was stirred for more one hour at the same temperature. The internal temperature was then raised further to 20 to 25° C., and the mixture was stirred for one hour. After this reaction, the mixture was added to an aqueous ammonium chloride solution (16 g, 60 ml) prepared beforehand in another 3″ diameter flask at 10° C. or less to carry out quenching. Acetone (220 ml) was added thereto, the internal temperature was raised to 50 to 65° C., and dissolution was carried out, followed by separation. The organic layer of the upper layer was then collected and cleaned with an aqueous 5% sodium hydrogencarbonate solution at the same temperature. The solvent was evaporated so as to be concentrated to about 50 ml. After cooled to an internal temperature of 2 to 10° C., a precipitated crystal was filtered. The filtered crystal was cleaned with toluene (10 ml) and dried to obtain a crystal of 3-m-nitrobenzoylindole (18.2 g) (80.0% yield).

1. stirringAfter stirring for two hours at the same temperature
2. customwas lowered to 0 to 5° C.
3. additionwas added at an internal temperature of 0 to 10° C.
4. customto synthesize iodeindole-1-ylmagnesium
5. customwas lowered to below −15° C
6. customThe slurry of the iodeindole-1-ylmagnesium prepared previously
7. customat −15 to −10° C.
8. stirringthe mixture was stirred for more one hour at the same temperature
9. temperatureThe internal temperature was then raised further to 20 to 25° C.
10. stirringthe mixture was stirred for one hour
11. customAfter this reaction
12. customprepared
13. customat 10° C. or less
14. customto carry out quenching
15. additionAcetone (220 ml) was added
16. temperaturethe internal temperature was raised to 50 to 65° C.
17. dissolutiondissolution
18. customfollowed by separation
19. customThe organic layer of the upper layer was then collected
20. customThe solvent was evaporated so as
21. concentrationto be concentrated to about 50 ml
22. temperatureAfter cooled to an internal temperature of 2 to 10° C.
23. filtrationa precipitated crystal was filtered
24. customdried