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Method for synthesizing 2,5-dimethoxy-4-chloroaniline

A technology of dimethoxyl and chloroaniline, applied in chemical instruments and methods, preparation of organic compounds, preparation of amino hydroxyl compounds, etc., can solve problems such as environmental pollution, complicated operation, reduction limitation, etc., and achieve low equipment investment and high reaction efficiency High selectivity and easy separation effect

Active Publication Date: 2016-05-25
LIAONING UNIVERSITY
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Problems solved by technology

Although the iron powder and alkali sulfide reduction method is widely applicable and the process is simple, it causes serious pollution to the environment during the reduction process. Although catalytic hydrogenation is a reduction method with a wide range of applications and high efficiency, when the substrate When containing other reducible sensitive groups, the reduction will be limited. In addition, the cost of this method is high and the operation is more complicated.
Although the electrolysis method has a high yield and does not pollute the environment, it consumes a lot of energy and is mostly used in laboratories and semi-industrial production
Due to the high cost of application of hydrazine hydrate, it is subject to certain restrictions

Method used

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  • Method for synthesizing 2,5-dimethoxy-4-chloroaniline

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Effect test

Embodiment 12

[0020] The synthesis of embodiment 12,5-dimethoxy-4-chloroaniline

[0021] In a 100ml autoclave equipped with a stirring bar, add 2,5-dimethoxy-4-chloronitrobenzene (10mmol), selenium powder (0.0158g), H 2 O (2ml), C 6 h 12 (40ml), NaHCO 3 (0.42g), feed carbon monoxide to 6MPa, then heat to 150°C and stir to react for 8 hours, put the autoclave in the air to cool naturally, stir and oxidize the product in the air for a period of time, then suction filter, and wash with distilled water for 2 to 3 After suction filtration, a white solid was obtained, which was the target product, and dried in the dark.

[0022] The white solid was detected: mp117~118℃.

[0023] 1 HNMR (300MHz, CDCl 3 )δ7.26(s,2H,NH 2 ), 6.79 (s, 1H, ArH skeleton), 6.37 (s, 1H, ArH skeleton), 3.80 (s, J=3.5Hz, 6H, CH 3 ).

[0024] The purity of the product detected by high performance liquid chromatography was 98.38%.

Embodiment 22

[0025] The synthesis of embodiment 22,5-dimethoxy-4-chloroaniline

[0026] Other experimental methods and conditions are the same as in Example 1, only the reaction temperature is changed, and the yield of 2,5-dimethoxy-4-chloroaniline is shown in Table 1.

[0027] Table 1

[0028] temperature(°C)

Embodiment 32

[0029] Synthesis of embodiment 32,5-dimethoxy-4-chloroaniline

[0030] Other experimental methods and conditions are the same as in Example 1, only the CO pressure is changed, and the yield of 2,5-dimethoxy-4-chloroaniline is shown in Table 2.

[0031] Table 2

[0032] Pressure (MPa)

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Abstract

The invention relates to a method for synthesizing 2,5-dimethoxy-4-chloroaniline. The method comprises the steps: in the presence of carbon oxide and water, performing the reaction in an organic solvent under a high temperature and high pressure by adopting 2,5-dimethoxy-4-chloro-nitrobenzene as a raw material, selenium as a catalyst and organic alkali or inorganic alkali as an assistant catalyst, and reducing the nitro to amino to synthesize the 2,5-dimethoxy-4-chloroaniline. The method adopts high-pressure reaction and one-pot reaction, so that less equipment investment is needed, the operation is simple and convenient, and a product is relatively easy to separate and purify.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to using 2,5-dimethoxy-4-chloronitrobenzene as a raw material, selenium as a catalyst, and an organic base or an inorganic base as a cocatalyst, under the conditions of the presence of carbon monoxide and water , In an organic solvent, a method for synthesizing 2,5-dimethoxy-4-chloroaniline under high temperature and high pressure. Background technique [0002] 2,5-Dimethoxy-4-chloroaniline is an important intermediate of organic pigments and pesticides, mainly used in coatings, inks, plastics, rubber, synthetic fibers and other industries, with excellent application properties. At present, in the process of nitro reduction, there are mainly the following methods: iron powder reduction, catalytic hydrogenation reduction, hydrazine hydrate reduction, alkali sulfide reduction and electrolytic reduction, etc. Although the iron powder and alkali sulfide reduction method is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/02
CPCC07C213/02C07C217/84
Inventor 刘晓智秦龙安萌佟健祖余洋刘云飞尹明娟
Owner LIAONING UNIVERSITY
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