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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).
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 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 reaction is thought to begin with the formation of a Schiff base, and then proceed via an intra-molecular condensation to make an imine intermediate (see below). There is then a loss of water that leads to a ring closing and formation of the quinoline derivative.
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]
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. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. [4]
The overall reaction type is a combination of both an addition reaction as well as a rearrangement reaction. This reaction was discovered by Max Conrad (1848–1920) and Leonhard Limpach (1852–1933) in 1887 while they were studying the synthesis of quinoline derivatives. [1] [2] The Conrad-Limpach synthesis
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).
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