[HP]

 
 Hello,

I think to try one synthesys in which isopropylamine:(CH3)2 CHNH2 reacts with succinic anhydride:(COCH2CH2CO)O in chlorophorm in the presence of pyridine base. I cant fully understand the role of the pyridine in such reaction- may be it plays the role of protection of the forming free carboxylic group from the succinic anhydride but i red from organic books that pyridine form salts only with strong acids and couldn't find such with the weak organic acids
If You have any suggestions pls help me

[Mitch]

It's a base, what do bases do?

[movies]

The effect could be two things:

First, pyridine may function as a base to partially deprotonate the amine so that it is more nucelophilic.  The pyridinium that results could then protonate the carboxylate that is formed after the amine attacks the anhydride.  This is necessary because you will ultimately lose water to form the succinimide.  Pyridine would essentially function as a proton shuttle.

Second, pyridine is a rather good nucleophile and if used in excess may react with the anhydride to make an acyl-pyridinium ion which is very, very reactive.  This ion could then be attacked by the amine.

[HP]

Thank you for the comprehensive answer.
I really wont to obtain a product with free carboxylic groups and if possible to escape succine imide formation or other side reactions so the role of pyridine must be essentual that. The product i dsire to obtain will be water soluble so now i think how best to isolate it from the organic chlorophorm phase. I also know the pyridine is moderate soluble in water but may be its less soluble in alakline solution..If anybody have suggestions how best isolate my product write pls