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Bucherer reaction

The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The reaction is widely used in the synthesis of dye precursors aminonaphthalenesulfonic acids.C10H7-2-OH + NH3 ⇌ C10H7-2-NH2 + H2O

Mechanism
In the first step of the reaction mechanism a proton adds to C2 or C4 of naphthol: : This dearomatization occurs at the expense of 25 kcal/mol. In the next step, bisulfite adds to C3, leading to the sulfonic acid. Displacement of sulfonate group by the amine gives naphthylamine. The amination is reversible. The reaction is summarized as follows: : The Bucherer carbazole synthesis is a related reaction. == References ==
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