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

[Hix3r]

I think you probably came across this, but then can you tell me, if you tried synthetising the product by this way? CoCl2, it says that it has great potential. Anyway I'm looking forward for the answer.

http://www.scielo.br/scielo.php?pid=...pt=sci_arttext