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Quinoline is a heterocyclic aromatic organic compound with the chemical formula C 9 H 7 N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown.
The formation of the quinoline product is influenced by the interaction of both steric and electronic effects.In a recent study, Sloop [8] investigated how substituents would influence the regioselectivity of the product as well as the rate of reaction during the rate-determining step in a modified Combes pathway, which produced trifluoromethylquinoline as the product.
The Skraup reaction. In this example, nitrobenzene serves as both the solvent and the oxidizing agent. The reaction, which otherwise has a reputation for being violent, is typically conducted in the presence of ferrous sulfate. [5] Arsenic acid may be used instead of nitrobenzene and the former is better since the reaction is less violent. [6]
The Knorr quinoline synthesis is an intramolecular organic reaction converting a β-ketoanilide to a 2-hydroxyquinoline using sulfuric acid. This reaction was first described by Ludwig Knorr (1859–1921) in 1886 [1] Knorr quinoline synthesis. The reaction is a type of electrophilic aromatic substitution accompanied by elimination of water.
The mechanism for the Gould–Jacobs reaction begins with a nucleophilic attack from the amine nitrogen follows by the loss of ethanol to form the condensation product. A 6 electron cyclization reaction with the loss of another ethanol molecule forms a quinoline (ethyl 4-oxo-4,4a-dihydroquinoline-3-carboxylate).
Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to ...
The reaction of isatin with a base such as potassium hydroxide hydrolyses the amide bond to give the keto-acid 2. This intermediate can be isolated, but is typically not. A ketone (or aldehyde) will react with the aniline to give the imine (3) and the enamine (4). The enamine will cyclize and dehydrate to give the desired quinoline (5).
This reaction is also known as the Skraup-Doebner-Von Miller quinoline synthesis, and is named after the Czech chemist Zdenko Hans Skraup (1850–1910), and the Germans Oscar Döbner (Doebner) (1850–1907) and Wilhelm von Miller (1848–1899).