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Isoniazide ramification and preparation method and application thereof

A technology of isoniazid and its derivatives, applied in the field of organic chemical synthesis, can solve the problems of high production cost and weak reactivity of ketone carbonyl, and achieve the effects of low production cost, easy preparation and high yield

Inactive Publication Date: 2018-09-14
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the medicinal limitations such as the toxic and side effects of the hydrazide group in isoniazid, compared with hydrazides, the condensation of free amino groups reduces the toxicity of hydrazides, and develops the application value of isoniazid hydrazide compounds. However, the reaction between ketone carbonyl and ammonia requires reflux, and at the same time, acid is added to the system as a catalyst, and the production cost is relatively high. Therefore, an efficient and green method is needed to solve the problem of weak reactivity of ketone carbonyl

Method used

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  • Isoniazide ramification and preparation method and application thereof
  • Isoniazide ramification and preparation method and application thereof
  • Isoniazide ramification and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0025] Add 0.0137g (0.1mmol) of isoniazid and 0.0234g (0.1mmol) of camphorsulfonic acid into a 25mL Erlenmeyer flask, add 3mL of a mixed solvent of ethanol and acetonitrile (v:v=1:1), shake to make it fully dissolve. After standing at room temperature for 2-3 days, 0.0358 g of colorless transparent crystals was obtained with a yield of 96.5%.

[0026] The crystals of the target product were analyzed by X-ray single crystal diffraction. Monochromatization of Mo Kα using graphite on a Bruker D8-ray diffractometer Radiation is used as a diffraction light source to collect diffraction intensity data for single crystals. The three-dimensional structure shows that the amino group of isoniazid and the ketone carbonyl group of camphorsulfonic acid form a C=N double bond after dehydration condensation Indicates the generation of target compounds, such as figure 1 shown.

[0027] The target product was analyzed by X-ray powder diffraction, such as figure 2 shown. The crystals ...

Embodiment 2

[0031] Add 0.0137g (0.1mmol) of isoniazid and 0.0234g (0.1mmol) of camphorsulfonic acid into a 25mL Erlenmeyer flask, add 3mL of a mixed solvent of methanol and acetonitrile (v:v=1:1), shake to make it fully dissolve. After standing at room temperature for 2-3 days, 0.0342 g of colorless transparent crystals was obtained with a yield of 92.2%.

[0032] The product was analyzed by X-ray single crystal diffraction, X-ray powder analysis and infrared analysis, confirming that the target product 2-(2-isonicotinylhydrazono)-7,7-dimethylbicyclo[2.2.1]heptane was synthesized Alk-1-yl-methanesulfonic acid.

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Abstract

The invention discloses isoniazide ramification and a preparation method and application thereof. According to the isoniazide ramification, isoniazide and medical intermediate camphorsulfonic acid which treat phthisic are taken as raw materials, a solvent evaporation method is adopted, and a target product is obtained at the indoor temperature. Compared with the common schiff base synthesis, during the production process, the solvent dosage is little, reaction conditions are mild, pollution on the environment is little, the production cost is low, the operation is simple, the control is easy,the preparation is easy, and the method is applicable to industrial production.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to the synthesis of isoniazid derivatives by a simple and mild dehydration method. Background technique [0002] Schiff bases are a class of compounds containing imine or amethinimine groups synthesized by the condensation reaction of amines and active carbonyl groups. Acylhydrazone modified by isoniazid structure is synthesized by the condensation reaction of hydrazide and aldehyde or ketone, and its structure contains carbonyl and imine groups (hydrazone) connected to the secondary amino group. Because the structure contains >C=N-functional groups, it also belongs to the category of Schiff bases. [0003] Isoniazid, also known as Remifen, is a commonly used specific drug for the treatment of tuberculosis. It is an important drug with high efficiency and low toxicity for the clinical treatment of various tuberculosis. limitation. The amino group at the end of isoniaz...

Claims

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Application Information

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IPC IPC(8): C07D213/86A61P31/06
CPCC07D213/86A61P31/06
Inventor 郭放韩洋
Owner LIAONING UNIVERSITY
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