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Azo coupling of diazonium salts

2 real reactions from the literature, on anilines. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Azo coupling: anthranilic acid (an aniline) with 1) HCl / NaNO2; 2) N,N-dimethylaniline gives the azo compound. 64% yield.

  2. Azo coupling: 4-phenyl-1,2,5-oxadiazol-3-amine (an aniline) and mesitylene (an alkylbenzene) with 1) NOBF4; 2) mesitylene, heat gives the azo compound. 90% yield.