Mechanism
in the first step of the reaction mechanism a proton adds to a carbon atom with high electron density therefore by preference to C2 or C4 of naphthol (1). This leads to resonance stabilized adducts 1a-1e.
De-aromatization of the first ring of the naphthalene system occurs at the expense of 25 kcal/mol. In the next step a bisulfite anion adds to C3 through 1e. This results in the formation of 3a which tautomerizes to the more stable 3b to the sulfonic acid of tetralone. A nucleophilic addition follows of the amine with formation of 4a and its tautomer 4b loses water to form the resonance stabilized cation 5a. This compound is deprotonated to the imine 5b or the enamine 5c but an equilibrium exists between both species. The enamine eliminates sodium bisulfite with formation of naphthylamine 6.
It is important to stress that this is a reversible reaction. The reaction is summarized as follows:
The Bucherer carbazole synthesis is a related reaction.
Read more about this topic: Bucherer Reaction
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