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Method for producing 3-substituted-oxy-4-pyridazinol derivative

一种制造方法、羟基哒嗪的技术，应用在有机化学等方向，能够解决未具体公开等问题，达到高选择率的效果

Active Publication Date: 2012-06-20
MITSUI CHEM AGRO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this manufacturing method is only a formal description and has not been specifically disclosed.

Method used

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  • Method for producing 3-substituted-oxy-4-pyridazinol derivative
  • Method for producing 3-substituted-oxy-4-pyridazinol derivative
  • Method for producing 3-substituted-oxy-4-pyridazinol derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] Production of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-hydroxypyridazine

[0154] To a mixture of 13.0 g (87.0 mmol) of 2-cyclopropyl-6-methylphenol and 1,2-dichlorobenzene (78.3 mL) was added 3.67 g (87.0 mmol) of 95% sodium hydroxide at room temperature. The mixture was heated up to 180° C., stirred and refluxed for 30 minutes to perform azeotropic dehydration. A solution of 5.00 g (purity 95.7%, 29.0 mmol) of 4-hydroxy-3,6-dichloropyridazine prepared in advance in tert-butanol (95.0 g) was added dropwise to the obtained solution at 180° C. over 5 hours. (Tert-butanol was distilled off while adding dropwise.) Then, stirred at 180° C. for 2 hours, then cooled the reaction solution to room temperature, added 78.7 g of pure water, stirred for 30 minutes, and separated 2-cyclocyanide containing excessively added Organic phase of propyl-6-methylphenol. 50.0 g of toluene was added to the aqueous phase, stirred at room temperature for 30 minutes, and the organic phase ...

Embodiment 2

[0156] Production of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-hydroxypyridazine

[0157] To a mixture of 13.0 g (87.0 mmol) of 2-cyclopropyl-6-methylphenol and 1,2-dichlorobenzene (78.3 mL) was added 3.67 g (87.0 mmol) of 95% sodium hydroxide at room temperature. The mixture was heated up to 180° C., stirred and refluxed for 30 minutes to perform azeotropic dehydration. A solution of 5.00 g (purity 95.7%, 29.0 mmol) of 4-hydroxy-3,6-dichloropyridazine prepared in advance in tert-butanol (95.0 g) was added dropwise to the obtained solution at 180° C. over 10 hours. (Tert-butanol was distilled off while adding dropwise.) Then, after stirring at 180° C. for 30 minutes, the reaction liquid was cooled to room temperature, 78.7 g of pure water was added, stirred for 30 minutes, and 2-cyclopropane containing excessively added was separated. The organic phase of base-6-methylphenol. 50.0 g of toluene was added to the aqueous phase, stirred at room temperature for 30 minutes, and...

Embodiment 3

[0159] Production of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-hydroxypyridazine

[0160] To a mixture of 12.8 g (86.4 mmol) of 2-cyclopropyl-6-methylphenol and 1,2-dichlorobenzene (78.3 mL) was added 3.64 g (86.4 mmol) of 95% sodium hydroxide at room temperature. The mixture was heated up to 180° C., stirred and refluxed for 30 minutes to perform azeotropic dehydration. A solution of 5.00 g (purity 95%, 28.8 mmol) of 4-hydroxy-3,6-dichloropyridazine prepared in advance in tert-butanol (95.0 g) was added dropwise to the obtained solution at 180° C. over 2 hours. (Tert-butanol was distilled off while adding dropwise.) Then, stirred at 180° C. for 30 minutes, then cooled the reaction solution to room temperature, added 78.7 g of pure water, stirred for 30 minutes, and separated 2-cyclocyanide containing excessively added Organic phase of propyl-6-methylphenol. 50.0 g of toluene was added to the aqueous phase, stirred at room temperature for 30 minutes, and the organic phase...

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Abstract

The disclosed method for producing a 3-substituted-oxy-4-pyridazinol derivative represented by general formula I is characterized by reacting a compound represented by general formula III and a compound represented by general formula IV under the presence or absence of a base, and the presence or absence of a solvent. Through this method, it is possible to produce the 3-substituted-oxy-4-pyridazinol derivative represented by general formula I with high efficiency and highly selectively.

Description

technical field [0001] The present invention relates to a method for producing 3-substituted oxy-4-hydroxypyridazine derivatives useful as drugs, agricultural chemicals, functional materials, or intermediates thereof. The present invention also relates to a method for producing 3-substituted oxy-4-pyridazinyl 4-morpholine carboxylate using the 3-substituted oxy-4-hydroxypyridazine derivative. Background technique [0002] The 3-substituted oxy-4-hydroxypyridazine derivatives of the present invention are useful as drugs, agricultural chemicals, functional materials or intermediates thereof. For example, 3-phenoxy-4-hydroxypyridazine derivatives are known to have herbicidal activity (Patent Document 1). In addition, it is known that ester derivatives of 3-phenoxy-4-hydroxypyridazine compounds have the same herbicidal activity (Patent Document 1). As an example of this compound, 3-phenoxy-4-pyridazinyl 4-morpholine carboxylate is described (Patent Document 1). [0003] As a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/16
CPCC07D237/16C07D401/12C07D403/12
Inventor 生岛英明近藤信弘高田威塚本芳久吉冨英武三田晴子
Owner MITSUI CHEM AGRO INC
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