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The Skraup synthesis is a chemical reaction used to synthesize quinolines.It is named after the Czech chemist Zdenko Hans Skraup (1850-1910). In the archetypal Skraup reaction, aniline is heated with sulfuric acid, glycerol, and an oxidizing agent such as nitrobenzene to yield quinoline.
Both groups claimed the synthesis of a 12 membered diazaannulene (structure 1) from an N-aryl pyridinium chloride and an amine, an aniline in the case of the Japanese group (depicted below) and an aliphatic amine (anticipating surfactant properties) in the case of the American group.
The reaction was first used by Antoine Béchamp to reduce nitronaphthalene and nitrobenzene to naphthylamine and aniline, respectively. [3] The Béchamp reduction is broadly applicable to aromatic nitro compounds. [4] [5] Aliphatic nitro compounds are however more difficult to reduce, often remaining as the hydroxylamine. Tertiary aliphatic ...
This compound can be prepared by the reduction of nitrobenzene with zinc in the presence of NH 4 Cl. [1] [2] Alternatively, it can be prepared by transfer hydrogenation of nitrobenzene using hydrazine as an H 2 source over a rhodium catalyst. [3]
A modern synthesis entails reduction of nitrobenzene to phenylhydroxylamine (C 6 H 5 NHOH) which is then oxidized by sodium dichromate (Na 2 Cr 2 O 7). [5] Nitrosobenzene can also be prepared by oxidation of aniline using peroxymonosulfuric acid (Caro's acid) [6] or potassium peroxymonosulfate under biphasic conditions. [7]
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C 6 H 5 NO 2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline.
In terms of its physical properties, 4,4'-benzidine is poorly soluble in cold water but can be recrystallized from hot water, where it crystallises as the monohydrate. It is dibasic, the deprotonated species has K a values of 9.3 × 10 −10 and 5.6 × 10 −11. Its solutions react with oxidizing agents to give deeply coloured quinone-related ...
Gould-Jacobs reaction starting from an aniline and ethyl ethoxymethylenemalonate; Skraup synthesis using ferrous sulfate, glycerol, aniline, nitrobenzene, and sulfuric acid. A number of other processes exist, which require specifically substituted anilines or related compounds: Camps quinoline synthesis using an o-acylaminoacetophenone and ...