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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 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 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.
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] Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found ...
The Combes quinoline synthesis is a chemical reaction, which was first reported by Combes in 1888. Further studies and reviews of the Combes quinoline synthesis and its variations have been published by Alyamkina et al ., [ 1 ] Bergstrom and Franklin, [ 2 ] Born, [ 3 ] and Johnson and Mathews.
The reaction mechanism is not exactly known; two proposals are presented here. One possibility is at first an aldol condensation, starting from the enol form of the pyruvic acid (1) and the aldehyde, forming an β,γ-unsaturated α-ketocarboxylic acid (2). This is followed by a Michael addition with aniline to form an aniline derivative (3).
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 ...
In this study 4-isopropylaniline 1 is reacted with a mixture (50:50)of ordinary pulegone and the 13 C-enriched isomer 2 and the reaction mechanism is outlined in scheme 2 with the labeled carbon identified with a red dot. The first step is a nucleophilic conjugate addition of the amine with the enol to the amine ketone 3 in a reversible reaction.
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