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Method for preparing 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene

A pyridyl and ethoxy technology, applied in the field of preparing 4-[2-ethoxy] nitrobenzene, can solve the problems of easy occurrence of safety accidents, high risk, explosive reactions, etc., and achieves improved production safety, The effect of reducing pollution and reducing production costs

Inactive Publication Date: 2018-05-08
白银京宇新药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sodium hydride is too dangerous when used in industrial production, and it will react explosively when it meets water. At the same time, when using sodium hydride, it will produce a large amount of hydrogen gas that is discharged unorganized, which is very prone to safety accidents

Method used

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  • Method for preparing 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene
  • Method for preparing 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve 150g of 2-(5-ethyl-2-pyridyl)ethanol in 450g of dichloromethane, add 150g of solid sodium hydroxide (96%) and 7.5g of 75% trioctylmethyl ammonium chloride, control Temperature 0-5°C, add dropwise 150g p-fluoronitrobenzene / 150g dichloromethane solution, keep warm at 0-5°C for 4 hours after the addition, after the reaction is completed, add 300g water dropwise at 0-5°C, stir for 5 minutes , standing and stratifying, the organic layer was washed three times with 200g*3 water, washed once with 100g saturated brine, dried by adding 10g of anhydrous magnesium sulfate, decolorized by adding 5g of activated carbon, filtered, the filtrate was concentrated to dryness under reduced pressure, added 300g of petroleum ether 0-5 Keep warm at ℃ for 2 hours, filter, and dry at 30-40℃ to get 254g of 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene, yield: 94.0%, HPLC purity : 99.2%.

Embodiment 2

[0022] Change 150g solid sodium hydroxide (96%) into 150g90% solid potassium hydroxide in embodiment 1, other operations are the same, get 4-[2-(5-ethyl-2-pyridyl) ethoxy] nitro Benzene 249g, yield: 92.2%, HPLC purity: 99.1%.

Embodiment 3

[0024] Change 150g solid sodium hydroxide (96%) into 150g solid potassium carbonate in Example 1, separate by column chromatography, and other operations are the same to obtain 4-[2-(5-ethyl-2-pyridyl)ethoxy ] Nitrobenzene 63g, yield: 23.3%, HPLC purity: 99.7%.

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Abstract

The invention relates to a method for preparing 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene. The method is characterized by comprising the following steps: dissolving 2-(5-ethyl-2-pyridyl)ethyl alcohol in halohydrocarbon, adding inorganic alkali and a phase transfer catalyst, then adding fluoronitrobenzene, controlling a reaction temperature within 0 to 50 DEG C, controlling reaction time to be4 hours, and performing separation and purification to obtain the 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene. The inorganic alkali such as sodium hydroxide with high safety replaces bibliographic sodium hydride, and the halohydrocarbon such as dichloromethane is used as a solvent, so that the high-quality 4-[2-(5-ethyl-2-pyridyl)ethyoxyl]nitrobenzene is synthesized according to a phase transfermethod; therefore, the production safety is greatly improved, pollution of a solvent such as DMF to the environment is relieved, and the production cost is reduced.

Description

technical field [0001] The invention belongs to the field of pharmaceutical intermediates, in particular to a method for preparing 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene. Background technique [0002] Pioglitazone hydrochloride indication II diabetic patients, a variety of synthetic methods have been reported in the literature, and there are two mainstream synthetic routes: [0003] One, EP 257 78 1, Chem. Pharm. Bull. 39 (6) 1440 1445 (1991), EP 506 273, WO93 / 13095 and EP 816 340 have reported that pioglitazone hydrochloride is prepared by the ene reduction route, and the specific reaction formula is as follows: [0004] [0005] The last step of reduction in this method requires a large amount of Pd / C or catalytic reduction with cobalt chloride. A large amount of palladium carbon leads to high product cost and cannot be industrialized. When cobalt chloride is used for catalytic reduction, heavy metal cobalt residues are not easy to remove, which is harmful to hum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/30
CPCC07D213/30
Inventor 熊传辉李耀勇高兴发
Owner 白银京宇新药业有限公司