Separation

[Nucleophile]

Hey all!

I'm having a little trouble with some syntheses in the lab and thought I'd come here to ask you guys, considering a lot of you seem pretty knowledgeable.

Anyways, we are synthesizing N-aryl enamino esters using N-methylaniline + methyl acetoacetate and an acid catalyst. We have created a mixture of basically 50% N-methylaniline and 50% product. However, we cannot seem to separate the product from the N-methylaniline!!! We have tried column chromatography with various solvents and solvent gradients, recrystallization, and even vacuum distillation. No matter what we try, the N-methylaniline seems to be staying there (or the compound is breaking apart into its original components as we try to separate it).

If you have any ideas on a better method of separation or synthesis, please please PLEASE let me know.

Thanks!
Nucleophile