当前位置: X-MOL 学术Synlett › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
O-(2,4-Dinitrophenyl)hydroxylamine
Synlett ( IF 1.7 ) Pub Date : 2014-04-03 , DOI: 10.1055/s-0033-1341110
Zhanhui Yang

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]).

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.



中文翻译:

O-(2,4-二硝基苯基)羟胺

O-(2,4-二硝基苯基)羟胺(1)是橙色固体(mp = 112°C)[1],当暴露在空气中时相当稳定。它是可商购的并且可以容易地通过德沙雷特的方法大规模合成的:[1]由2,4-二硝基氯苯的亲核芳族取代Ñ -hydroxyphthalimide随后肼解给出了1,收率94%,经两个步骤(方案[1] )。

作为一种亲电胺化试剂,1用于向各种C-,N-和O-亲核体提供一个游离的NH 2基团,以提供在合成化学和药物化学中均具有重要意义的产物。副产物为2,4-二硝基苯酚(流程[2])。具有1的胺化具有反应条件温和,操作简单安全的优点以及广泛的底物范围。

更新日期:2014-04-03
down
wechat
bug