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Preparation method of 4-ethylpyridine

A technology of ethylpyridine and acetylpyridine, applied in organic chemistry and other fields, can solve problems such as difficult industrialization and dangerous processes

Inactive Publication Date: 2019-03-29
郑州长宽科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the cost of this method is low, 4-vinylpyridine is easy to polymerize. This method is difficult to implement industrialization and is a dangerous process.

Method used

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  • Preparation method of 4-ethylpyridine
  • Preparation method of 4-ethylpyridine
  • Preparation method of 4-ethylpyridine

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[0029] The invention provides a kind of preparation method of 4-ethylpyridine, comprises the following steps:

[0030] (1) After mixing ethyl 4-pyridinecarboxylate and sodium ethoxide, heat it to 90-110°C, then add ethyl acetate dropwise to carry out Claisen ester condensation reaction to obtain 3-oxo 3-(4-pyridyl ) ethyl propionate;

[0031] (2) After mixing the ethyl 3-oxo 3-(4-pyridyl)propionate obtained in the step (1), dimethyl sulfoxide and water, heat treatment is carried out to obtain 4-acetylpyridine;

[0032] (3) Mix ethylene glycol and potassium hydroxide and cool, add hydrazine hydrate, heat up to 60-80°C, then mix with the 4-acetylpyridine obtained in the step (2), and perform a reduction reaction to obtain 4-acetylpyridine base pyridine.

[0033] In the present invention, after mixing ethyl 4-pyridinecarboxylate and sodium ethoxide, heat it to 90-110°C, then add ethyl acetate dropwise to carry out Claisen ester condensation reaction to obtain 3-oxo 3-(4-pyridyl...

Embodiment 1

[0061] (1) Preparation of ethyl 4-pyridinecarboxylate

[0062] 0.8 mol of isonicotinic acid, 0.64 mol of absolute ethanol, 2.0 g of activated powdered activated carbon were successively added into a 100 mL three-necked flask as a catalyst, and toluene as a solvent. Microwave reaction time 10min (power 200W; temperature 130°C). with saturated Na 2 CO 3 The aqueous solution was used to neutralize the reaction solution until the pH was 7, and the layers were allowed to stand to separate, and the upper organic layer was taken; the aqueous phase was extracted with 20 mL of chloroform, and the extract and the organic layer were combined. Chloroform was first recovered by atmospheric distillation and then vacuum distillation to obtain colorless transparent liquid ethyl 4-pyridinecarboxylate with a purity of 96.3% (GC) and a yield of 97.2%.

[0063] Activated powdered activated carbon is obtained by immersing the powdered activated carbon in 60 mL of 25% p-toluenesulfonic acid aque...

Embodiment 2

[0071] (1) Preparation of ethyl 4-pyridinecarboxylate

[0072] 0.8 mol of isonicotinic acid, 0.64 mol of absolute ethanol, 2.0 g of activated powdered activated carbon were successively added into a 100 mL three-necked flask as a catalyst, and toluene as a solvent. Microwave reaction time 10min (power 200W; temperature 130°C). with saturated Na 2 CO 3 The aqueous solution was used to neutralize the reaction solution until the pH was 7, and the layers were allowed to stand to separate, and the upper organic layer was taken; the aqueous phase was extracted with 20 mL of chloroform, and the extract and the organic layer were combined. Chloroform was first recovered by atmospheric distillation and then vacuum distillation to obtain colorless transparent liquid ethyl 4-pyridinecarboxylate with a purity of 96.3% (GC) and a yield of 97.2%.

[0073] Activated powdered activated carbon is obtained by immersing the powdered activated carbon in 60 mL of 25% p-toluenesulfonic acid aque...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a preparation method of 4-ethylpyridine. The preparation method of the 4-ethylpyridine comprises the following stepsof: mixing ethyl 4-picolinate with sodium ethoxide, heating to 90 to 110 DEG C, then dropwise adding ethyl acetate, and carrying out claisen condensation reaction, thus obtaining ethyl 3-oxo-3-(4-pyridyl) propionate; mixing the ethyl 3-oxo-3-(4-pyridyl) propionate, dimethyl sulfoxide and water, and carrying out heating treatment, thus obtaining 4-acetylpyridine; cooling after mixing glycol with potassium hydroxide, adding hydrazine hydrate, rising the temperature to 60 to 80 DEG C, then mixing with the 4-acetylpyridine, and carrying out reduction reaction, thus obtaining the 4-ethylpyridine.The 4-ethylpyridine prepared through the preparation method provided by the invention is higher in yield and purity.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 4-ethylpyridine. Background technique [0002] Ethylpyridine is the starting material for the synthesis of many drugs, especially the intermediates in the synthesis of many insecticide drugs, but there is no report on the industrial production of 4-vinylpyridine. [0003] At present, the commonly used methods for preparing 4-ethylpyridine in the laboratory are: [0004] (1) In the presence of iron powder or zinc powder, pyridine is alkylated with acetic anhydride to obtain 4-ethylpyridine. This method needs to consume a large amount of acetic acid in the reaction process, and needs to consume a large amount of salt of wormwood when separating the product simultaneously, not only aftertreatment is more difficult, and the yield of the 4-ethylpyridine that obtains is also lower, about 35%~ 45.5%. [0005] (2) 4-vinylpyridine is subjected to high-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/24
CPCC07D213/24
Inventor 吕海宽刘兵张海洋杜自飞郑超超
Owner 郑州长宽科技有限公司
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