[gizzi007]

Hi guys,

I am a graduate student and trying to make the following compound:
Phenylimine, this the condition I used:
1mmol of Aniline, 3mmol of Formalin and 3mmol Glacial acetic acid at reflux.

I analyzed the residue by GC-MS and TLC all indicated presence of large of amounts of aniline M.Wt=93g/mol. I did column separation 4:1 Pet.ether: E.acetate but the yield was very low.

I wonder if you guys have any solution for this problem.

Thanks

[rolnor]

Have you checked the literature?

[rolnor]

I have worked with imines and they are not stable on silica gel, I think you could add some pyridine when packing the silica column to avoid hydrolysis, also your compound could be even more unstable then the ones I made from aliphatic amine and aromatic aldehydes.

[clarkstill]

I agree with everything Rolnor has said - this imine doesn't look very stable at all.

This paper forms the HCl salt, which might be a better bet, although experimental details are lacking:

J. Heterocyclic Chem., 48, 829 (2011)

[gizzi007]

Thank you guys for your replies. I tried different conditions, Dean Stark trap to get rid of water but it didn't work out. Finally, I was able to produce the phenylimine. GC-MS: M/Z= 105 . I repeated the reaction by adding only a catalytic amount of AcOH which was very less than the quantity that I used to use. I think it was the reason for the rxn failure.

I performed two reactions, the only difference between them was the temperature. The scheme is attached.

Thank you again!