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Phenylhydrazine was the first hydrazine derivative characterized, reported by Hermann Emil Fischer in 1875. [7] [8] He prepared it by reduction of a phenyl diazonium salt using sulfite salts. Fischer used phenylhydrazine to characterize sugars via formation of hydrazones known as osazones with the sugar aldehyde. He also demonstrated in this ...
Hydrazines (R 2 N−NR 2) are a class of chemical compounds with two nitrogen atoms linked via a covalent bond and which carry from one up to four alkyl or aryl substituents. . Hydrazines can be considered as derivatives of the inorganic hydrazine (H 2 N−NH 2), in which one or more hydrogen atoms have been replaced by hydrocarbon grou
The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions.
When derived from hydrazine itself, hydrazones condense with a second equivalent of a carbonyl to give azines: [11] R 2 C=N−NH 2 + R 2 C=O → R 2 C=N−N=CR 2 + H 2 O. Hydrazones are intermediates in the Wolff–Kishner reduction. Hydrazones are reactants in hydrazone iodination, the Shapiro reaction, and the Bamford–Stevens reaction to ...
The Olin Raschig process is a chemical process for the production of hydrazine.The main steps in this process, patented by German chemist Friedrich Raschig in 1906 and one of three reactions named after him, are the formation of monochloramine from ammonia and hypochlorite, and the subsequent reaction of monochloramine with ammonia towards hydrazine. [1]
Hydrazine is an inorganic compound with the chemical formula N 2 H 4.It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour.Hydrazine is highly hazardous unless handled in solution as, for example, hydrazine hydrate (N 2 H 4 ·xH 2 O).
Since the reaction requires a free carbonyl group, only "reducing sugars" participate. Sucrose, which is nonreducing, does not form an osazone. A typical reaction showing the formation of an osazone. D-glucose reacts with phenylhydrazine to give glucosazone. The same product is obtained from fructose and mannose. General steps in osazone formation
An applied example is a synthesis of sunitinib begins by mixing 5-fluoroisatin slowly into hydrazine hydrate. [9] After 4 hours at 110 °C, the indole ring structure has been broken into (2-amino-5-fluoro-phenyl)-acetic acid hydrazide with reduction of the ketone at the 3-position.