Skraup Reaction

The Skraup synthesis is the reaction between anilines and glycerol in the presence of sulfuric acid and an oxidizing agent to deliver the corresponding quinolines.

Skraup Reaction

Skraup Reaction

Reaction Mechanism

Skraup Reaction
Skraup Reaction

1. The glycerol is dehydrated to form acrolein. 2. Nucleophilic conjugate addition of the amine. 3. Tautomerization. 4. Intramolecular electrophilic addition; ring closure. 5. Rearomatization and elimination affords dihydroquinoline.
6. Final oxidation with nitrobenzene delivers the quinoline.

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