Succinic anhydride yields the cyclic imide succinimide when heated with ammonium chloride at 200°C. Propose a mechanism for this reaction.

Question

The reaction of cyclohexanone and N,N-dimethylamine with sodiumtriacetoxyborohydride (NaBH(OAc)3) in methanol with acetic acid (AcOH) affords N,Ndimethylcyclohexanamine in high yield. However, if anhydrous HCl is used the reaction yield of N,Ndimethylcyclohexanamine is low and a side reaction occurs to produce alcohol. Draw a reaction mechanism for the reductive amination sequence, highlighting tautomers present in the reaction.

Answer 1

Question

Chapter 21.SE, Problem 39MP

Interpretation Introduction

Interpretation:

Succinic anhydride yields the cyclic imide succinimide when heated with ammonium chloride at 200°C. Propose a mechanism for this reaction.

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