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Method for preparing hydroxylamine through nitro-reduction

A technology of phenylhydroxylamine and hydroxylamine, which is applied in the field of preparation of hydroxylamine by reduction of nitro groups, can solve the problems of harsh preparation reaction conditions and inapplicability to large-scale production, and achieve the effects of mild reaction conditions, cheap raw materials, and high yield

Inactive Publication Date: 2014-02-19
大连九港生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, under the conditions of these nitro group reductions, the generated hydroxylamine can be rapidly continued to be reduced to amine, and by-products such as azo, hydrazo and azo oxide are easily generated, and the preparation reaction conditions are relatively harsh, and hydrogenation reduction requires Use of dangerous high-pressure devices, flammable hydrogen, toxic heavy metals or harmful chemical reagents, etc.
[0003] At the same time, there are also some reports in the literature that microwave or bio-fermentation methods are used to prepare hydroxylamine, but it is not suitable for large-scale production

Method used

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  • Method for preparing hydroxylamine through nitro-reduction
  • Method for preparing hydroxylamine through nitro-reduction
  • Method for preparing hydroxylamine through nitro-reduction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] The synthesis of embodiment 1 N-(2-chlorophenyl) hydroxylamine

[0014]

[0015] Add 48.2g of o-chloronitrobenzene (0.3mol, 98%, 1.0eq), 360g of ethanol, 360g of 1,2-dichloroethane, and 8g of Raney Ni into a 1L jacketed kettle equipped with mechanical stirring, a thermometer and an air duct , 2g of tetrabutylammonium bromide, start stirring; raise the temperature to 15°C, start to add hydrazine hydrate 46.9g (0.75mol, 80%, 2.5eq) dropwise, after the dropwise addition, continue to keep warm for 4h; after the reaction is complete, filter the reaction solution , the filtrate was rotary evaporated, and the residue of the kettle was recrystallized by adding ethanol to obtain 32.3 g of N-(2-chlorophenyl) hydroxylamine, with a yield of 75%.

Embodiment 2

[0016] The synthesis of embodiment 2 N-(4-methoxyphenyl) hydroxylamine

[0017]

[0018] Add 46.8g (0.3mol, 98%, 1.0eq) of 4-methoxynitrobenzene, 720g of ethanol, 10g of Raney Ni, and tetrabutylammonium bromide into a 1L jacketed kettle equipped with mechanical stirring, a thermometer and an air duct 1g, start stirring; raise the temperature to 25°C, start to dropwise add 37.5g of hydrazine hydrate (0.6mol, 80%, 2.0eq), after the dropwise addition, continue to keep warm for 4h; Ethanol was added for recrystallization to obtain 27.1 g of N-(4-methoxyphenyl) hydroxylamine with a yield of 65%.

Embodiment 3

[0019] Example 3 Synthesis of N-hydroxyl-N-2-[(N-p-chlorophenyl)-3-pyrazolyloxymethyl]aniline

[0020]

[0021] Add 100.9g (0.3mol, 98%, 1.0eq) of 2-[N-p-chlorophenyl]-3-pyrazolyloxy]nitrobenzene into a 1L jacketed kettle equipped with mechanical stirring, a thermometer and an air duct , 720g of isopropanol, 15g of Raney Ni, 0.8g of tetrabutylammonium bromide, start stirring; raise the temperature to 15°C, start to add 75g of hydrazine hydrate (0.75mol, 50%, 2.5eq) dropwise, after the dropwise addition is completed, continue to keep warm for 4h After the reaction is complete, the reaction solution is filtered, the filtrate is rotary evaporated, and the residue of the kettle is recrystallized by adding ethanol to obtain a light yellow solid product N-hydroxyl-N-2-[(N-p-chlorophenyl)-3-pyrazolyloxymethyl Base] aniline 80.5g, yield 85%.

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Abstract

The invention discloses a method for preparing hydroxylamine through nitro-reduction and belongs to the technical field of reduction of organic nitro compounds in the organic chemistry. According to the method for preparing the hydroxylamine through the nitro-reduction, substituted nitrobenzene reacts with hydrazine, and N-phenylhydroxylamine is prepared under the catalysis of Raney Ni. According to the method, used raw materials are cheap and easy to obtain, reaction conditions are mild, the yield is higher, and the selectivity is good, so that the method is a synthetic method with the significant industrial value.

Description

technical field [0001] The invention discloses a method for preparing hydroxylamine through nitro reduction, which belongs to the technical field of reduction of organic nitro compounds in organic chemistry. Background technique [0002] Phenylhydroxylamines are a class of important compounds, they are the key synthetic intermediates of many fine chemicals, pesticides and medicines. The usual preparation method is to reduce the corresponding nitrobenzene compounds through hydrogen transfer or hydrogenation to achieve the purpose of preparing hydroxylamine. However, under the conditions of these nitro group reductions, the generated hydroxylamine can be rapidly continued to be reduced to amine, and by-products such as azo, hydrazo and azo oxide are easily generated, and the preparation reaction conditions are relatively harsh, and hydrogenation reduction requires Use dangerous high-voltage devices, flammable hydrogen, toxic heavy metals or harmful chemical reagents, etc. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/00C07C239/10C07C239/12C07D231/22
Inventor 李雨王海英王荣良于圣慧李殿虎
Owner 大连九港生物科技有限公司
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