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Methoxy aniline compound and synthesis method thereof

A technology for methoxyaniline and 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 limited compatibility of functional groups, and achieve simple reaction conditions and convenient operation Effect

Active Publication Date: 2021-05-18
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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  • Methoxy aniline compound and synthesis method thereof
  • Methoxy aniline compound and synthesis method thereof
  • Methoxy aniline compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-16

[0028] Step 1: Add nitro compounds (see Table 1 for specific substances) and methanol into the reaction vessel, respectively add reducing agent (see Table 1 for specific substances), photocatalyst (see Table 1 for specific substances), water (see Table 1 for specific materials) 1), organic acid (see Table 1 for specific substances), and organic solvent (see Table 1 for specific substances) are added to the reaction vessel.

[0029] Step 2: uniformly heat the reaction vessel (such as heating in an oil bath) to the temperature described in Table 1 and irradiate under blue light, the nitro compound and methanol react in the solvent, and continue for the time described in Table 1; The reaction atmosphere that needs to be explained is argon protection.

[0030] Step 3: Purification step.

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

Embodiment 11

[0035] The nuclear magnetic data of embodiment 11 product is 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 embodiment 12 products 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 invention mainly relates to a preparation method of anisidine. According to the technical scheme, under the promotion of the photocatalyst and blue light, in the argon atmosphere, nitro compounds and methanol generate methoxyaniline, wherein products and additional products with stable molecular structures and excellent chemical properties are prepared, wherein a photocatalyst and a blue light source are used in the method, and a new path is provided for synthesis of methoxyaniline compounds. The method has the characteristics of mild reaction conditions, simple reaction system, less reaction equipment, simplicity and convenience in experimental operation and the like. The methoxyaniline derivative and the synthetic method thereof can be applied to a plurality of industrial production fields of dyes, pesticides, medicines, rubber additives and the like. The method is particularly suitable for scientific research, development and utilization of efficient and selective synthesis of methoxyaniline compounds by a one-pot method.

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, spices, plastics, pesticides, medicines, rubber additives, etc. For example: in the dye industry, it can be used to produce acid ink blue G, acid medium BS, reactive brilliant red X-SB and Jinguanghong, etc.; in the pesticide industry, it can be used to produce many insecticides and fungicides such as DDV, fenben, and toxachlor, etc. ; used in the manufacture of rubber additives such as anti-aging agent A, anti-aging agent D, accelerator M and CA; it can also be used as a raw material for pharmaceutical sulfonamides, as a stabilizer in explosives and as an anti-knock agent in gasoline; others can also be used For the manufacture of hydroquinone, 2-p...

Claims

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Application Information

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Patent Type & Authority Applications(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