反应详情

o-Nitrobenzylamine hydrochloride (20.4 g., 0.114 mole) was dissolved in a minimum volume of water and the solution was made strongly basic by addition of 10% sodium hydroxide. The clear oil which formed was extracted into two 120-ml. portions of ether. The ether was dried with 10 g. of anhydrous sodium sulfate, filtered, and finally dried over Drierite. The dried solution was filtered and evaporated, leaving a yellow oil. The oil was dissolved in 100 ml. of absolute ethanol and 11.4 g (0.114 mole) of freshly distilled ethyl acrylate was added. This solution was allowed to stand overnight and the solvent removed by distillation from a steam-cone. The oily residue was dissolved in 200 ml. of dry ether, the solution was cooled in an ice bath, and treated with dry hydrogen chloride. When precipitation was complete, the solid was filtered and dissolved in 120 ml. of boiling absolute ethanol. The hydrochloride crystallized from this solution on cooling yielding 20.7 g. of the aminopropionate hydrochloride, m.p. 137.5°-139.0°. By concentrating and cooling the mother liquor, an additional 5 g. was obtained, m.p. 136.5°-138.5°, and by repeating this operation 1.1 g., m.p. 136°-139°, was obtained, raising the total yield to 26.8 g. (81.4%). The analytical sample was prepared by repeated crystallization from absolute ethanol to give a melting point of 138.5°-139.0°.

1. customThe clear oil which formed
2. extractionwas extracted into two 120-ml
3. dry with materialThe ether was dried with 10 g
4. filtrationof anhydrous sodium sulfate, filtered
5. dry with materialfinally dried over Drierite
6. filtrationThe dried solution was filtered
7. customevaporated
8. customleaving a yellow oil
9. dissolutionThe oil was dissolved in 100 ml
10. customthe solvent removed by distillation from a steam-cone
11. dissolutionThe oily residue was dissolved in 200 ml
12. temperatureof dry ether, the solution was cooled in an ice bath
13. additiontreated with dry hydrogen chloride
14. customWhen precipitation
15. filtrationthe solid was filtered
16. dissolutiondissolved in 120 ml
17. customThe hydrochloride crystallized from this solution
18. temperatureon cooling
19. customyielding 20.7 g
20. concentrationBy concentrating
21. temperaturecooling the mother liquor
22. customwas obtained
23. custom, m.p. 136°-139°, was obtained
24. temperatureraising the
25. customtotal yield to 26.8 g
26. customThe analytical sample was prepared
27. customcrystallization from absolute ethanol
28. customto give a melting point of 138.5°-139.0°