Benzyne formation

Diazotization-decarboxylation of Anthranilic acid (2-aminobenzoic acid)

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Diazotization of anthranilic acid prodcues a diazonium salt which can lose nitrogen and carbon dioxide to produce benzyne. Evidence for this rather unlikely looking intermediate is provided by the fact that it can be trapped in a Diels-Alder reaction. The benzyne intermediate also appears in the aromatic substitution reactions.