(Doebner-Miller Synthesis, Doebner-von Miller Quinoline Synthesis, Skraup-Doebner-von Miller Quinoline Synthesis)
Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Doebner-Miller Reaction. Comprehensive Organic Name Reactions and Reagents. 198:924–929.
- Published Online: 15 SEP 2010
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The Doebner–Miller reaction is an acidic condensation between primary aromatic amines (e.g., anilines) and α,β-unsaturated carbonyl compounds (mostly α,β-unsaturated aldehydes) to give 2,3-disubstituted quinolines. The optimal condition of this reaction is to heat the mixture of aniline/aldehyde (1:2) at 100°C for 6 h with hydrochloric acid and zinc chloride; in addition, an oxidizing reagent is also needed in this reaction, such as nitrobenzene. This reaction is generally used for the synthesis of quinolines with substituents on the pyridinoid ring.
- hydrochloric acid;
- zinc chloride;