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A kind of methoxyaniline compound and synthetic method thereof

A technology of methoxyaniline and nitro compounds, which is applied in the field of methoxyaniline compounds and their synthesis, can solve the problems of complex synthesis steps, poor atom economy, and large functional group compatibility limitations, and achieve group positioning and selection Good performance, shortened reaction steps, and shortened production cycle

Active Publication Date: 2022-05-27
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the methods for synthesizing such compounds have complex synthetic steps, poor atom economy and limited functional group compatibility, often requiring pre-functionalization of starting materials

Method used

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  • A kind of methoxyaniline compound and synthetic method thereof
  • A kind of methoxyaniline compound and synthetic method thereof
  • A kind of methoxyaniline compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-16

[0028] Step 1: the nitro compound (see Table 1 for specific materials) and methanol are added to the reaction vessel, and respectively reducing agent (see Table 1 for specific materials), photocatalyst (see Table 1 for specific materials), water (see Table for specific feeding amounts) 1), organic acid (refer to Table 1 for specific substances), and organic solvent (refer to Table 1 for concrete substances) are added to the reaction vessel.

[0029] Step 2: the reaction vessel is uniformly heated (such as oil bath heating) to the temperature described in Table 1 and irradiated under blue light, and the nitro compound and methanol are reacted in a solvent for the time described in Table 1; It should be noted that argon protection is selected for this reaction atmosphere.

[0030] Step 3: Purification step.

[0031] Table 1: Molar ratio and reaction temperature of nitro compounds to methanol, reducing agent, photocatalyst, water, organic organic acid, organic solvent (nitro com...

Embodiment 11

[0035] The nuclear magnetic data of the product of Example 11 are as follows:

[0036] 1 H NMR (400MHz, Chloroform-d) δ6.91-6.88(m, 2H), 6.58(d, J=7.9Hz, 1H), 3.84(s, 3H), 3.78(br, 2H); 13 C NMR (100MHz, Chloroform-d) δ147.8, 135.2, 123.6, 115.7, 113.7, 109.5, 55.6.

Embodiment 12

[0037] The nuclear magnetic data of the product of Example 12 are as follows:

[0038] 1 H NMR (400MHz, DMSO-d 6 )δ6.96(d,J=2.5Hz,1H),6.77-6.71(m,3H),4.84(br,2H),3.64(s,4H); 13 C NMR (100MHz, Chloroform-d) δ152.7, 137.7, 117.4, 116.7, 115.0, 109.6, 55.9.

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Abstract

The present invention mainly relates to a kind of preparation method of methoxyaniline. Under the promotion of photocatalyst and blue light, the present invention realizes the technical scheme of generating methoxyaniline from nitro compounds and methanol in an argon atmosphere. Products with stable molecular structure and excellent chemical properties and their additional products are prepared. In this method, photocatalysts and blue light sources are used to provide a new route for the synthesis of methoxyaniline compounds. It has the characteristics of mild reaction conditions, simple reaction system, less reaction equipment, and convenient experimental operation. The methoxyaniline derivative and its synthesis method of the present invention can be used in many industrial production fields such as dyes, pesticides, medicines, rubber additives, etc.; it is especially suitable for the scientific research of one-pot efficient and selective synthesis of methoxyaniline compounds and development.

Description

technical field [0001] The invention relates to a methoxyaniline compound and a synthesis method thereof, belonging to the field of organic synthesis. Background technique [0002] Methoxyaniline and its derivatives are an important class of organic compounds. Aniline plays an important role in the industrial production of dyes, fragrances, plastics, pesticides, medicines, and rubber auxiliaries. For example: in the dye industry, it can be used to make acid ink blue G, acid medium BS, reactive brilliant red X-SB and golden red, etc.; in the pesticide industry, it can be used to produce many insecticides, fungicides such as DDV, herbicide, chlorfenapyr, etc. ;Used in the manufacture of anti-aging agent A, anti-aging agent D, accelerator M and CA and other rubber auxiliaries; can also be used as a raw material for pharmaceutical sulfonamides, and can be used as a stabilizer in explosives, and an anti-explosion agent in gasoline; Others can also be used For the manufacture of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/84C07C213/00C07C213/10C07C225/22C07C221/00C07C255/59C07C253/30C07C253/34
CPCC07C217/84C07C213/00C07C213/10C07C225/22C07C221/00C07C255/59C07C253/30C07C253/34
Inventor 黄华文钟帅邓国军肖福红陈善平
Owner XIANGTAN UNIV