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Preparation methods for important intermediates of anthranilic diamide compound

A technology of o-formamidobenzamide and compounds, which is applied in the field of chemical synthesis, can solve the problems of complex operation, low yield, long reaction time, etc., and achieve the effect of simple operation process, high product purity and good product purity

Inactive Publication Date: 2012-07-18
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the product yield of this technology is low, and after cooling to room temperature, no solid is precipitated, and a large amount of solvent extraction is required, which increases the cost and complicates the operation
[0011] Above-mentioned method (1), (2) reaction time is longer, and productive rate is lower; And in method (3), operation is more complicated, needs a large amount of solvent extraction, and yield is lower, and production cost is higher

Method used

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  • Preparation methods for important intermediates of anthranilic diamide compound
  • Preparation methods for important intermediates of anthranilic diamide compound
  • Preparation methods for important intermediates of anthranilic diamide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1: Preparation of 2-hydrazino-3-chloropyridine (II)

[0033] Add 2,3-dichloropyridine (14.8g, 0.1mol) and 1,4-dioxane (120mL) into a reaction flask with a stirrer, and stir to dissolve at room temperature. After completely dissolving, pour into the reaction flask Slowly add 75ml (1.2mol) of 80% hydrazine hydrate dropwise, and drop it within 1 hour. At this time, the solution becomes clear, then the reaction system is heated to reflux state, reacted for 6 hours, and monitored with a TLC plate until the raw material 2,3- Dichloropyridine disappeared, stopped heating, cooled down to room temperature, and a light gray solid precipitated out. After suction filtration, washing with water and drying, 14.2 g of 2-hydrazino-3-chloropyridine solid was obtained, with a yield of 96% and a purity of 98%.

Embodiment 2

[0034] Embodiment 2: Preparation of 2-hydrazino-3-chloropyridine (II)

[0035] Add 2,3-dichloropyridine (14.8g, 0.1mol) and tetrahydrofuran (120mL) into a reaction flask with a stirrer, start stirring at room temperature until completely dissolved, then slowly add 80% hydrated Hydrazine 75ml (1.2mol), dripped in 1 hour, then the reaction system was heated to reflux state, reacted for 12 hours, monitored with TLC board until the raw material 2,3-dichloropyridine disappeared, stopped heating, cooled down to room temperature, A light gray solid was precipitated. After suction filtration, water washing and drying, 12.1 g of 2-hydrazino-3-chloropyridine solid was obtained, with a yield of 82% and a purity of 98%.

Embodiment 3

[0036] Embodiment 3: Preparation of 2-hydrazino-3-chloropyridine (II)

[0037] Add 2,3-dichloropyridine (14.8 g, 0.1 mol) and absolute ethanol (120 mL) into a reaction flask with a stirrer, and start stirring to dissolve at room temperature. After completely dissolving, slowly add 80% 75ml (1.2mol) of hydrazine hydrate was dropped within 1 hour, and the solution became clear at this time, then the reaction system was heated to reflux state, reacted for 6 hours, and monitored with a TLC plate until the disappearance of the raw material 2,3-dichloropyridine, Heating was stopped, cooled down to room temperature, and a light gray solid precipitated out. After suction filtration, washing with water and drying, 10.4 g of 2-hydrazino-3-chloropyridine solid was obtained, with a yield of 70% and a purity of 98%.

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Abstract

The invention discloses preparation methods for important intermediates of an anthranilic diamide compound, particularly relates to intermediates 2-hydrazino-3-chloropyridine and 1-(3-chloro-2-pyridy)-3-pyrazolidone-5-acetylenecarboxylate and belongs to the technical field of chemical synthesis methods. The preparation method for 2-hydrazino-3-chloropyridine comprises the following steps of: refluxing 2,3-dichloropyridine used as a raw material in hydrazine hydrate and an organic solvent for 6 to 12 hours, and cooling to crystallize to obtain 2-hydrazino-3-chloropyridine. The preparation method for 1-(3-chloro-2-pyridy)-3-pyrazolidone-5-acetylenecarboxylat comprises the following steps of: adding organic solvent and corresponding alkali into 2-hydrazino-3-chloropyridine, adding diethyl maleate, after the raw material disappears, adding glacial acetic acid and refluxing for half an hour, and cooling to obtain white 1-(3-chloro-2-pyridy)-3-pyrazolidone-5-acetylenecarboxylate. By adopting the technology, the yield of 2-hydrazino-3-chloropyridine can reach over 95 percent, and the purity of 2-hydrazino-3-chloropyridine can reach over 95 percent; the yield of 1-(3-chloro-2-pyridy)-3-pyrazolidone-5-acetylenecarboxylate reaches over 70 percent, and the purity of 1-(3-chloro-2-pyridy)-3-pyrazolidone-5-acetylenecarboxylate can reach over 98 percent; and a process is simple, raw materials can be obtained easily, the yield is high, and the purity of a product is high, and the preparation methods are suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis methods, and specifically relates to two important intermediates of o-formamidobenzamide compounds, 2-hydrazino-3-chloropyridine and 1-(3-chloro-2-pyridyl)- The preparation method of ethyl 3-pyrazolidinone-5-carboxylate. Background technique [0002] Many heterocyclic compounds have been gradually developed into ultra-efficient pesticides in modern research and development. Nitrogen-containing heterocycles have become the focus of research, especially pyridine and pyrazole rings. Studies have found that if the carboxylic acid part of the o-formamidobenzamide compound is transformed into a pyridylpyrazole carboxylic acid, its activity will be much higher than that of other carboxylic acids. [0003] Chlorantraniliprole is an o-formamidobenzamide compound developed by DuPont. It still has quite good insecticidal activity at very low mass concentration, and has broad spectrum, long resi...

Claims

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Application Information

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IPC IPC(8): C07D213/77C07D401/04
Inventor 李刚
Owner EAST CHINA UNIV OF SCI & TECH
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