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O-hydroxyaniline derivative and preparation method thereof

A technology for o-hydroxyaniline and derivatives, which is applied in the field of o-hydroxyaniline derivatives and their preparation, can solve the problems of complex synthesis methods and low efficiency of aniline compounds, and achieves high synthesis efficiency, broad application prospects and simple preparation methods. Effect

Active Publication Date: 2016-06-01
ANHUI NORMAL UNIV
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  • Abstract
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  • Claims
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Problems solved by technology

[0007] However, the synthesis method of aniline compounds in the prior art is complex and inefficient

Method used

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  • O-hydroxyaniline derivative and preparation method thereof
  • O-hydroxyaniline derivative and preparation method thereof
  • O-hydroxyaniline derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] A kind of o-hydroxyaniline derivative, its structural formula is:

[0033]

[0034] A preparation method of o-hydroxyaniline derivatives, comprising the following steps:

[0035] (1) With 820mmol sodium hydride as a catalyst, 200mmol diethyl malonate and 440mmol propargyl bromide were added to 250mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry, and use ethyl acetate:petroleum ether column chromatography with a volume ratio of 1:100 to obtain a white solid product, namely compound 1;

[0036] (2) Mix 80mmol of compound 1 with 200mmol of phenylethynyl bromide in 1.09mmol of Pd (PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 340mmol triethylamine as base, with 200ml anhydrous acetonitrile as solvent, stirring and reacting at room temperature for 12 hours, the product was washed w...

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Abstract

The invention discloses an o-hydroxyaniline derivative and a preparation method thereof. Compared with the prior art, the invention provides a synthetic method of an o-hydroxyaniline derivative to generate a series of novel o-hydroxyaniline derivatives. Compared with existing o-hydroxyaniline derivatives, the o-hydroxyaniline derivative prepared by the invention is polycyclic, has more complex and diversified structure that is more complex and diversified, prevails among pharmaceutical intermediates, functional materials and farmland pharmaceuticals, is widely applied in the fields such as molecular machinery, materials chemistry and supramolecular chemistry, and also has a more promising application prospect in chemical production and clinical medicine; moreover, the preparation method provided by the invention is simple and is high in synthetic efficiency.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an o-hydroxyaniline derivative and a preparation method thereof. Background technique [0002] At present, amine compounds are widely used. Amino groups in organic compounds can be changed into other groups through diazotization reaction, and they are important organic chemical raw materials. Amines can be used to synthesize pesticides, dyes and pigments, medicines, rubber additives, synthetic resins, textile additives, surfactants, photosensitive materials and other organic and fine chemical raw materials and intermediates. [0003] The introduction of amino groups is often related to the function of fine chemicals. For example, the introduction of amino groups can lead to the red shift of compounds in the visible spectrum, which plays an important role in dye chemistry. The introduction of amino groups at the ortho position of the chromophoric group of dyes can ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22
CPCC07D333/22
Inventor 余娟胡益民
Owner ANHUI NORMAL UNIV
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