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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.
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).
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can be considered as derivatives of the inorganic hydrazine (H 2 N−NH 2), in which one or more hydrogen atoms have been replaced by hydrocarbon grou
Industrially the compound is produced by treatment of urea with hydrazine: [3] OC(NH 2) 2 + 2 N 2 H 4 → OC(N 2 H 3) 2 + 2 NH 3. It can also be prepared by reactions of other C1-precursors with hydrazine, such as carbonate esters. [2] It can be prepared from phosgene, but this route cogenerates the hydrazinium salt [N 2 H 5]Cl and results in ...
Hydrazine is used to convert the ester to an acylhydrazine, which is reacted with nitrous acid to give the acyl azide. Heating the azide in ethanol yields the ethyl carbamate via the Curtius rearrangement. Acid hydrolysis yields the amine from the carbamate and the carboxylic acid from the nitrile simultaneously, giving the product amino acid.
Hydrazinium azide decomposes explosively into hydrazine, ammonia, and nitrogen gas: [3] 12 N 5 H 5 → 3 N 2 H 4 + 16 NH 3 + 19 N 2. Crystallization with an equimolar amount hydrazine yields the solid hydrazinium azide hydrazinate, [N 2 H + 5] [N − 3] · [N 2 H 4], or N 7 H 9, as monoclinic crystals. This compound is less hygroscopic and less ...
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When derived from hydrazine itself, hydrazones condense with a second equivalent of a carbonyl to give azines: [10] 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 ...