反应详情

A suspension of 4.5 g. (0.0190 mole) of 4-benzoylindolin-2-one in 200 ml. of 3N sodium hydroxide was refluxed under a nitrogen atmosphere for 4 hr. The volume of water was reduced by approximately half, and the solution saturated with sodium chloride. The solution was chromatographed on a 230 ml. (wet volume) column of Amberlite XAD-2 ion exchange resin packed in distilled water. The product precipitated on the top of the column packing, but dissolved as the column was eluted with distilled water. The fractions containing the product were collected, combined, and the solvent removed under reduced pressure to give 4.6 g. of solid. Recrystallization from methanol-ether gave 0.91 g. of a yellow solid, m.p. 256.5°-258.5° C. (dec.). The filtrate was evaporated under reduced pressure and the residue was dissolved in hot isopropanol by adding a small amount of water. The hot solution was filtered to remove a suspended solid. The filtrate seeded and placed in the freezer for 12 hr. The pale yellow solid which separated was collected by filtration and yielded 2.84 g. (50.3%) of product, m.p. 254.5°-256° C. (dec.). A portion of the bulk product was dried under high vacuum at room temperature.

1. additionA suspension of 4.5 g
2. customThe solution was chromatographed on a 230 ml
3. customThe product precipitated on the top of the column packing
4. dissolutiondissolved as the column
5. washwas eluted with distilled water
6. additionThe fractions containing the product
7. customwere collected
8. customthe solvent removed under reduced pressure
9. customto give 4.6 g
10. customRecrystallization from methanol-ether
11. customgave 0.91 g
12. customThe filtrate was evaporated under reduced pressure
13. dissolutionthe residue was dissolved in hot isopropanol
14. additionby adding a small amount of water
15. filtrationThe hot solution was filtered
16. customto remove a suspended solid
17. customThe pale yellow solid which separated
18. filtrationwas collected by filtration
19. customyielded 2.84 g
20. customA portion of the bulk product was dried under high vacuum at room temperature