Question

Propose an arrow pushing mechanism for the reaction between 3-nitrophthalic acid and hydrazine to form the nitrohydrazide in the presence of water and triethylene glycol. This was asked for the Synthesis of a Chemiluminescence Compound: Luminol

Please label the structures and steps.

Also, please show arrows clearly so that it is understandble and easy to read and understand the mechanism.

Answer 1

Drawn below is the arrow push mechanism for the transformation of 3-nitrophthalic acid to nitrohydrazide.

Nucleophilic attack of hydroazine nitrogen on the carbonyl carbon center followed by protonation of O- give -OH. Reprotonation of -OH to form good leaving group H2O which leaves and gives an amide on one side. The process is repeated with reaction with second carboxylcia cid and NH2 of hydrazine to form the product as shown below.