Isopentyl nitrite acts as a source of NO ⁺ ions, reacting with primary amines to generate diazonium cations. Predict the major product of the following reaction sequence.

Step-by-step solution

The reaction of anthranilic acid (2-aminobenzoic acid) with isopentyl nitrite (a source of NO ⁺ ) converts the primary amine group into a diazonium salt, forming the zwitterionic intermediate benzenediazonium-2-carboxylate. Upon heating, benzenediazonium-2-carboxylate undergoes simultaneous loss of N ₂ and CO ₂ to generate benzyne, a highly reactive intermediate. Benzyne then undergoes a [4+2] cycloaddition (Diels-Alder reaction) with furan. In this reaction, furan acts as the diene ( 4 component) and benzyne acts