[Med90]

Plz anybody clear me the mechanism for the following reaction.
Its really hard for me, so need your help

Thanking you in advance

[n4k]

Where reactions?

[Med90]

hi n4k
thanks for your concern, the reaction is attached as pdf version. you can see after logging. Plz find it and hoping for your help.

[n4k]

why reaction not perfect? There is nitrogenium not balance

[Med90]

Sorry, Nitrogen is in balance. main thing is how comes 6 membered ring changed to five membered ring, I couldnt find the solution for that.
Any idea?

thanks

[macman104]

No, nitrogen is not in balance.  You have 5 on the left, and 4 on the right.  Where did you get this mechanism?  Are you sure it's complete?  Simply aqueous acid is all that is needed?

[intrepid_nerd]

this doesn't seem to make much sense, how did the exocyclic N come in?  is this missing a second stage perhaps?

[pizza1512]

Could you give us an idea of what context this reaction is being done for?

I can see that the reaction requires many stages; and might not even be just 'one' mechanism. I mean just by looking at the amine group; its difficult to see how that might be converted into a aldehyde in one step!

[spirochete]

Are you absolutely sure both reactant and product were copied down 100% correctly?

I came up with a very reasonable looking mechanism that breaks the ring, creates an aldehyde group and removes the exocyclic amine group, but the final product has connectivity that is slightly different from yours.

[Vidya]

I think reaction is incomplete or incorrect.You need to give us more steps.

[Mitch]

You are going to an aromatic system, in the product, so at least there is that.