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Skraup Synthesis

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Casual Chemistry

Synthesis of quinoline. Conjugate addition of aniline to the 1,4 position of acrolein. Mediated by acid. Cyclisation by electrophilic aromatic substitution on to an activated carbonyl group. After rearomatisation, water is eliminated likely by an E1 mechanism. The intermediate is then oxidised by a separate oxidising agent such as nitrobenzene.

posted by kolesomsa