[darkdevil]

Dear,

I am doing the formylation of this compounds using Vilesmeier Reagent (DMF + POCl3)
However, when doing NMR analysis I found the that aldehyde group was attached on the nitrogen atom instead of the aromatic ring.


I saw wikipedia demonstrated a similar reaction with Indole, and the reaction occurs at the ring. The only difference is that I used DMF as solvent while they used toluene. Does the solvent effect really that matter?


Thanks!

[discodermolide]

The solvent won't make much difference, usually you need traces of DMF. It's not surprising that it N-formylated, where did you expect to react?

[darkdevil]

I expect it to react at the aromatic ring

[discodermolide]

Perhaps you should try protecting the NH groups. Even then I am not convinced that it formylate the aromatic ring(s).