Michael Addition

Essay # 1952

Chemistry

Michael Addition

Synthesis of 1-phenyl-3-phenylaminopyrrolidine-2,5-dione

1,838 words () | 4 sources | 2001 United States

From the Paper:

"The preparation of 1-phenyl-3-phenylaminopyrrolidine-2,5-dione 5, a fused-ring heterocycle, is described. The synthesis of maleanilic acid 3, was completed with the reaction of maleic anhydride 1 with aniline 2. The resulting product maleanilic acid 3 was reacted with acetic anhydride to produce N-phenylmaleimide 4. N-phenylmaleimide 4 was then reacted with aniline 2 to produce 1-phenyl-3-phenylaminopyrrolidine-2,5-dione 5. The purification of all three compounds maleanilic acid 3, N-phenylmaleimide 4, and 1-phenyl-3-phenylaminopyrrolidine-2,5-dione 5 was achieved through filtration. The product maleanilic acid 3 was high in yield with 84.4% being recovered. N-phenylmaleimide 4 was mediocre in yield with only 68.0% being recovered. The final product, 1-phenyl-3-phenylaminopyrrolidine-2,5-dione 5,was high in yield with 85.8% obtained. The experiment was successful with the products being identified as maleanilic acid 3, N-phenylmaleimide 4, and 1-phenyl-3-phenylaminopyrrolidine-2,5-dione 5. The compounds were identified as such through their melting points, and spectral information obtained from IR, and 1H NMR."