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Preparation method of 2-(trifluoromethyl) pyridine-3-formaldehyde (I)

A technology of trifluoromethyl and pyridine, applied in the field of preparation of 2-pyridine-3-carbaldehyde, can solve the problems of expensive trifluoromethylation reagents, unsuitable for industrial application, less attention to preparation methods, etc., and achieves low cost , the effect of few steps and high product yield

Active Publication Date: 2019-04-16
浙江工业大学上虞研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 2-(trifluoromethyl)pyridine-3-carbaldehyde, whose structure is shown in formula (I), is an important chemical pesticide intermediate, and pyridines are key raw materials for the synthesis of azaindole, but currently Less attention has been paid to the preparation method, and the availability of pyridines is the key issue whether the drugs containing the azaindole skeleton can be produced industrially
However, the raw materials and trifluoromethylation reagents of this method are expensive and are not suitable for industrial applications.

Method used

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  • Preparation method of 2-(trifluoromethyl) pyridine-3-formaldehyde (I)
  • Preparation method of 2-(trifluoromethyl) pyridine-3-formaldehyde (I)
  • Preparation method of 2-(trifluoromethyl) pyridine-3-formaldehyde (I)

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Embodiment 1

[0022] Embodiment 1: the preparation of 3-iminopropene:

[0023] In a 500mL airtight four-necked reaction flask, add 56.1g of acrolein and 200mL of ethanol, stir evenly, control the temperature at 50°C, and slowly add 81.6g of 25% concentrated ammonia water dropwise for 1 hour. After the dropwise addition, Stirring was continued for 2 hours. After the reaction was completed, the product was distilled off under normal pressure to obtain 54.6 g of 3-iminopropene, with a yield of 99.1%.

Embodiment 2

[0024] Embodiment 2: the preparation of 3-iminopropene:

[0025] In a 500mL airtight four-necked reaction flask, add 56.1g of acrolein and 200mL of ethanol, stir evenly, control the temperature at 60°C, and slowly add 81.6g of 25% concentrated ammonia water dropwise for 1 hour. After the dropwise addition, Stirring was continued for 2 hours. After the reaction was completed, the product was distilled off under normal pressure to obtain 46.3 g of 3-iminopropene, with a yield of 84.0%.

Embodiment 3

[0026] Example 3: Preparation of 3-(1,3-dioxolan-2-yl)-2-trifluoromethylpyridine:

[0027] In a 500mL airtight four-necked reaction flask, add 55.1 grams of 3-iminopropene, 85.2 grams of piperidine, 184.10 grams of 3-(1,3-dioxolan-2-yl)-1,1,1-tri Fluoroacetone and 200mL ethanol, stirred evenly, controlled temperature at 60°C, reacted for 12 hours, after the reaction was completed, the solvent ethanol and catalyst piperidine were distilled off under reduced pressure to obtain off-white solid 3-(1,3-dioxolan-2-yl) - 136.4 grams of 2-trifluoromethylpyridine, yield 62.2%.

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Abstract

The invention discloses a preparation method of 2-(trifluoromethyl) pyridine-3-formaldehyde (I), and belongs to the technical field of preparation methods of chemical drug intermediates. Acrolein, ammonium hydroxide and 4,4,4-trifluoro-3-oxobutyraldehyde are used as raw materials, and the 2-(trifluoromethyl) pyridine-3-formaldehyde is prepared through aldimine condensation, cyclization and hydrolysis deprotection. The preparation method of the 2-(trifluoromethyl) pyridine-3-formaldehyde (I) has the advantages that the adopted raw materials are relatively cheap and easy to obtain, the method is simple and convenient to operate, the yield of the product is higher, and the industrialized value is higher.

Description

technical field [0001] The invention belongs to the technical field of preparation methods of chemical drug intermediates, and in particular relates to a preparation method of 2-(trifluoromethyl)pyridine-3-carbaldehyde. Background technique [0002] 2-(trifluoromethyl)pyridine-3-carbaldehyde, whose structure is shown in formula (I), is an important chemical pesticide intermediate, and pyridines are key raw materials for the synthesis of azaindole, but currently Less attention has been paid to the preparation method, and the availability of pyridine compounds is the key issue whether the drugs containing the azaindole skeleton can be produced industrially. [0003] Due to the unique properties of trifluoromethyl, the introduction of it into organic compounds can significantly change the acidity, dipole moment, polarity, lipophilicity, and chemical and metabolic stability of the compound. Therefore, compounds containing trifluoromethyl have been used in It is widely used in t...

Claims

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Application Information

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IPC IPC(8): C07D213/48
CPCC07D213/48
Inventor 方标许萌柯军梁
Owner 浙江工业大学上虞研究院有限公司
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