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Method for synthesizing 1,3-dichloro-6-trifluoromethyl-phenanthrene-9-formaldehyde

A trifluoromethyl, synthesis method technology, applied in the field of synthesis of 1,3-dichloro-6-trifluoromethyl-9-phenanthrene formaldehyde, can solve the problems of harsh conditions, low melting point, high anhydrous requirements, etc. Achieve the effects of mild and easy-to-control reaction conditions, simple process operation, and low anhydrous requirements

Inactive Publication Date: 2009-07-08
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Above method needs to use lead tetraacetate as oxygenant, has many shortcoming: 1, yield is not high, is about 78%, and product purity is poor, fusing point is on the low side; 2, lead tetraacetate waste residue and reaction waste residue all have a large amount of poisonous leaded Compounds, pollution control is difficult and costly; 3. Lead tetraacetate oxidation operation is difficult, conditions are harsh, water requirements are high, side reactions are many, and post-treatment is complicated

Method used

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  • Method for synthesizing 1,3-dichloro-6-trifluoromethyl-phenanthrene-9-formaldehyde
  • Method for synthesizing 1,3-dichloro-6-trifluoromethyl-phenanthrene-9-formaldehyde

Examples

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Effect test

Embodiment 1

[0019] Add 34.7 grams of 1,3-dichloro-6-trifluoromethyl-9-phenanthrene methanol (0.10 moles) and 800 milliliters of toluene to a 1000-milliliter four-neck flask with mechanical stirring, a thermometer, and a reflux condenser, and add 0.3 g cuprous chloride (3 mmol) and 0.6 g 1,10-phenanthroline (3 mmol), add 0.53 g diethyl hydrazine dicarboxylate (3 mmol) and 27.6 g potassium carbonate (0.20 mole) , stirring to raise the temperature, and slowly inject air at 60° C. for bubbling reaction for 40 hours. After the reaction is complete, filter, wash the filter cake with 3×100 ml of toluene, combine the toluene, concentrate the toluene under reduced pressure to 100 ml, cool to below 20°C, and precipitate the product 1,3-dichloro-6-trifluoromethyl-9 -Phenanthrene formaldehyde was filtered and dried to obtain a yellowish white solid, which was dried to obtain 28.0 g of the product with a yield of 81.1%. Melting point 185.5~185.8℃, content 99.5% (HPLC).

Embodiment 2

[0021] The operation of Example 1 was repeated, only the cuprous chloride in Example 1 was changed to 0.4 gram of cuprous bromide (2.8 mmol), and the reaction time was 30 hours to obtain a product yield of 80.5%.

Embodiment 3

[0023] The operation of Example 1 was repeated, the reaction temperature in Example 1 was increased to 80° C., and the reaction time was 20 hours to obtain a product yield of 79.5%.

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Abstract

The invention relates to a preparation method of an intermediate of phenanthrene methanol antimalarial drugs. The existing method needs to use lead tetraacetate as an oxidant, and the pollution control is difficult and costly; the reaction conditions are harsh, the requirement for anhydrous is high, there are many side reactions, and the post-treatment is complicated. The present invention is characterized in that 1,3-dichloro-6-trifluoromethyl-9-phenanthrene methanol is used as a catalyst with copper salt, and air is an oxidant, and in the presence of an organic solvent with 1,10-phenanthroline and hydrazine Diethyl formate is oxidized to give 1,3-dichloro-6-trifluoromethyl-9-phenanthrene aldehyde. The invention is a green and environment-friendly preparation method with mild and easy-to-control reaction conditions, no toxicity, and high product purity and yield.

Description

technical field [0001] The invention relates to a preparation method of 1,3-dichloro-6-trifluoromethyl-9-phenanthrene formaldehyde, an intermediate of phenanthrene methanol antimalarial drugs. Background technique [0002] Phenanthrene methanol antimalarial drugs are a class of effective malaria treatment drugs. As schizonticides, they have high killing activity against asexual endoerythrocytic Plasmodium. It is clinically used to treat single or mixed acute malaria caused by Plasmodium falciparum or Plasmodium vivax infection. Its representative drugs include halofantrine, debutylhalofantrine and so on. The structural formula of phenanthrene methanol antimalarial drugs is as follows: [0003] [0004] Wherein R1 is hydrogen, methyl, ethyl, propyl, butyl, R2 is methyl, ethyl, propyl, butyl, phenyl, HX is hydrochloric acid, tartaric acid, oxalic acid, maleic acid. [0005] The key intermediate of phenanthrene methanol antimalarial drugs is 1,3-dichloro-6-trifluoromethyl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/29C07C47/55
Inventor 商志才钱洪胜孟建波陈云陈洪光
Owner ZHEJIANG UNIV
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