反应详情

The triamine trihydrochloride of 4-aminophenylalanine (0.188 g, 0.65 mmol) was dissolved in 15 mL of anhydrous methanol, and solid potassium hydroxide (0.89 g, 0.44 mmol), was added to the solution. The resultant suspension was stirred at room temperature for 1 hour, and thereafter refrigerated overnight. The suspension was filtered, the solid (potassium chloride) was discarded, and the clear pale yellow filtrate was added dropwise, with stirring, to a reaction vessel containing lanthanum(III) acetate hydrate (0.110 g, 0.32 mmol) in 40 mL of anhydrous methanol. The resultant mixture was stirred at room temperature for 15 min and then 2,6-diacetylpyridine (0.104 g, 0.65 mmol) was added. The mixture was heated under reflux conditions for 14 hours; the orange colored solution thereby produced was filtered to remove a small amount of unreacted europium acetate and evaporated to dryness under reduced pressure at 60° C. in a rotary evaporator. The gummy residue was repeatedly worked up in diethyl ether, ultimately yielding a solid product. This solid was taken up in warm chloroform and filtered. The insoluble residue was discarded, and the yellow-orange filtrate was gradually diluted with diethylether and chilled. The precipitate thus formed was filtered, dissolved in anhydrous methanol, and added dropwise with stirring to approximately 300 mL of chilled anhydrous diethylether. The pale yellow powdery solid thus formed was filtered off, washed with diethylether, and dried in vacuo over phosphorous pentoxide. Yield: 58%. Microanalysis and spectral data (IR, 1H and 13C NMR) confirmed the structure and purity of the product.

1. customrefrigerated overnight
2. filtrationThe suspension was filtered
3. additionthe clear pale yellow filtrate was added dropwise
4. temperatureThe mixture was heated under reflux conditions for 14 hours
5. customthe orange colored solution thereby produced
6. filtrationwas filtered
7. customto remove a small amount of unreacted europium acetate
8. customevaporated to dryness under reduced pressure at 60° C. in a rotary evaporator
9. customultimately yielding a solid product
10. filtrationfiltered
11. additionthe yellow-orange filtrate was gradually diluted with diethylether
12. temperaturechilled
13. customThe precipitate thus formed
14. filtrationwas filtered
15. dissolutiondissolved in anhydrous methanol
16. additionadded dropwise
17. stirringwith stirring to approximately 300 mL of chilled anhydrous diethylether
18. customThe pale yellow powdery solid thus formed
19. filtrationwas filtered off
20. washwashed with diethylether
21. dry with materialdried in vacuo over phosphorous pentoxide