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Synthesis method of 2-(3-chloropyridine-2-yl)-5-hydroxy-3-pyrazolidine ethyl formate

A kind of technology of ethyl pyrazolidine carboxylate and synthetic method, which is applied in the field of synthesis of ethyl 2--5-hydroxy-3-pyrazolidine carboxylate, can solve the problems of low yield and achieve safe and reliable synthesis without difficulty The effect of mild decomposition and reaction conditions

Inactive Publication Date: 2019-11-22
江苏优普生物化学科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yields are lower

Method used

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  • Synthesis method of 2-(3-chloropyridine-2-yl)-5-hydroxy-3-pyrazolidine ethyl formate
  • Synthesis method of 2-(3-chloropyridine-2-yl)-5-hydroxy-3-pyrazolidine ethyl formate

Examples

Experimental program
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Effect test

example 1

[0026] A 1000ml four-necked bottle with a stirring device is installed in a water bath, and the water bath is filled with iced brine. Add 100.5 g of glacial acetic acid (98%, 1.64 mol) and 250 g of n-butanol to the four-neck flask, stir, and add 81.2 g of 3-chloro-2-aminopyridine (98.3%, 0.621 mol). Another 45.6g (98.5%, 0.651mol) of sodium nitrite was dissolved in 57g of water, added to the constant pressure funnel, and connected to the above-mentioned four-necked bottle. When the temperature in the four-necked bottle drops to -2~-5°C, add the sodium nitrite solution in the constant pressure funnel dropwise into the four-necked bottle. Control the temperature in the bottle between -5 and 10°C. After the dropwise addition, keep warm at about 0°C. Check that the content of 3-chloro-2-aminopyridine is <0.5%. After the reaction is over, add about 1.8g of urea to starch-KI The test paper does not change color.

example 2

[0028] A 1000ml four-necked bottle with a stirring device is installed in a water bath, and the water bath is filled with iced brine. 109.5 g (98.8%, 0.621 mol) of diethyl succinate was added to the four-necked flask. Get two constant pressure funnels and add 30% ammonia water and the diazo solution of Example 1 respectively, and connect to the four-necked bottle. When the temperature in the four-necked bottle drops below 0°C, add ammonia water and diazo solution to the four-necked bottle at the same time, keep the temperature in the four-necked bottle at -5-15°C, and pH 4-6.5, keep warm after the addition Insulate at 0-15°C, take samples, after HPLC detects that the diazonium salt disappears, change to water bath heating, add ammonia water dropwise to pH 9-10.5, keep at 30-95°C for 2 hours, cool down to room temperature, add glacial acetic acid and to pH 6.5. Transfer the material in the four-necked bottle to a separatory funnel and let it stand for one hour. The organic p...

example 3

[0030] A 1000ml four-necked bottle with a stirring device is installed in a water bath, and the water bath is filled with iced brine. Add 101.2g (98%, 1.65mol) of glacial acetic acid and 250g of n-butanol to the four-necked flask, stir, and add 81.3g (98.3%, 0.622mol) of 3-chloro-2-aminopyridine. Another 82.2 g (82.0%, 0.654 mol) of n-butyl nitrite in n-butanol was added to the constant pressure funnel. When the temperature in the four-necked bottle drops to -2~-5°C, add n-butyl nitrite in the constant pressure funnel dropwise into the four-necked bottle. Control the temperature in the bottle between -5 and 10°C. After the dropwise addition, keep warm at about 0°C. Check that the content of 3-chloro-2-aminopyridine is <0.5%. After the reaction is over, add about 1.9g of urea to starch-KI The test paper does not change color.

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Abstract

The invention discloses a synthesis method of 2-(3-chloropyridine-2-yl)-5-hydroxy-3-pyrazolidine ethyl formate, which comprises the following steps: dissolving 3-chloro-2-aminopyridine in a mixed solution of an organic acid or inorganic acid and a solvent A, and carrying out diazotization at -5 to 10 DEG C in the presence of a diazotization reagent to obtain a diazonium solution; dropwise adding the obtained diazonium liquid into diethyl succinate (diethyl n-succinate) for reaction, and adding alkali and preserving heat in the reaction.. Through the route of diazotization, coupling and cyclization, the reaction conditions are mild; meanwhile, the diazonium salt of the 3-chloro-2-aminopyridine is relatively stable and is not easy to decompose and explode, and the synthesis is safe and reliable. Metal sodium or sodium ethoxide is not used, so that the safety risk in the synthesis process is reduced. The yield of the target product can reach 72% or above and is higher than that of a current common process method.

Description

technical field [0001] The invention relates to a method for synthesizing ethyl 2-(3-chloropyridin-2-yl)-5-hydroxyl-3-pyrazolidinecarboxylate. Background technique [0002] The structural formula of ethyl 2-(3-chloropyridin-2-yl)-5-hydroxy-3-pyrazolidinecarboxylate is as follows: [0003] [0004] Chlorantraniliprole (chlorantraniliprole) is the first insecticide in the o-formamidobenzamide compounds developed by DuPont (world patent WO0170671, Chinese patent CN1419537B, US patent US6747047), and has been used in more than 100 countries in the world It is sold in 3 countries, covering almost all major markets in the world. It is the largest insecticide in the global pesticide market since 2012 and the third largest insecticide for rice. The global sales in 2016 were 1.365 billion US dollars; 2011-2016 The compound annual growth rate is as high as 15.1%. Ethyl 2-(3-chloropyridin-2-yl)-5-hydroxy-3-pyrazolidinecarboxylate is an important intermediate in the synthesis of ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 张继钱施云云王任伟李红梅顾佳林
Owner 江苏优普生物化学科技股份有限公司
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