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DOI: 10.1055/s-0033-1341110
O-(2,4-Dinitrophenyl)hydroxylamine
Publikationsverlauf
Publikationsdatum:
03. April 2014 (online)
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Introduction
O-(2,4-Dinitrophenyl)hydroxylamine (1) is an orange solid (mp = 112 °C)[1] and fairly stable when exposed to air. It is commercially available and can be readily synthesized by Charette’s method on a large scale:[1] Nucleophilic aromatic substitution of 2,4-dinitrochlorobenzene by N-hydroxyphthalimide followed by hydrazinolysis gives 1 in 94% yield over two steps (Scheme [1]).
![](https://www.thieme-connect.de/media/synlett/201408/thumbnails/i_v0475_s1_10-1055_s-0033-1341110.gif)
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As an electrophilic amination reagent, 1 is used to donate a free NH2 group to a variety of C-, N-, and O-nucleophiles to give products of significant importance in both synthetic and medicinal chemistry. The byproduct is 2,4-dinitrophenol (Scheme [2]). Amination with 1 features the advantages of mild reaction conditions, simple and safe operations, and wide substrate scope.
![](https://www.thieme-connect.de/media/synlett/201408/thumbnails/i_v0475_s2_10-1055_s-0033-1341110.gif)
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