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Method for simply and effectively removing 2-position methyl and 6-position methyl of 2, 6-dimethyl-4-pyridinone derivative

A technology of pyridone and derivatives, applied in the field of removal of 2, can solve the problems of high reaction temperature, strong alkali, strong acid, etc., and achieve the effect of low volatility, few experimental steps and high chemical selectivity

Inactive Publication Date: 2013-03-13
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, the existing one-step and step-by-step demethylation methods for the 2- and 6-positions of pyridine all have some disadvantages, such as the need for high reaction temperatures and the use of excessive strong bases and strong acids.

Method used

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  • Method for simply and effectively removing 2-position methyl and 6-position methyl of 2, 6-dimethyl-4-pyridinone derivative
  • Method for simply and effectively removing 2-position methyl and 6-position methyl of 2, 6-dimethyl-4-pyridinone derivative

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Effect test

example 1

[0018] Add 2,6-dimethyl-4-oxo-N,1-di-p-tolyl-1,4-dihydropyridine-3-carboxamide (346 mg, 1.0 mmol) and anhydrous FeCl to a 25 mL round bottom flask 3 (195mg, 1.2mmol), and 2.0mL DMF, react in an oxygen (1.0atm) atmosphere, the reaction process is monitored by LC-MS, after the reaction, the system is naturally cooled to room temperature, and 20mL of water is added to the reaction system and stirred at room temperature. An insoluble solid precipitated out and was suction filtered, and the insoluble solid was purified by column chromatography to obtain 4-oxo-N,1-di-p-tolyl-1,4-dihydropyridine-3-carboxamide (232 mg, 73%).

[0019] 4-Oxo-N, 1-di-p-tolyl-1, 4-dihydropyridine-3-carboxamide

[0020] Colourless crystal.mp: 195-197℃; Yield: 73%, 1 H NMR (400MHz, CDCl 3 )δ12.33(s, 1H), 8.80(d, J=2.5Hz, 1H), 7.66(dd, J=7.8, 2.6Hz, 1H), 7.63(d, J=8.6Hz, 2H), 7.34( d, J=8.4Hz, 2H), 7.29(d, J=8.5Hz, 2H), 7.15(d, J=8.2Hz, 2H), 6.71(d, J=7.5Hz, 1H), 2.43(s, 3H), 2.33(s, 3H). 13 C NMR (100M...

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Abstract

The invention provides a method for simply and effectively removing 2-position methyl and 6-position methyl of a 2, 6-dimethyl-4-pyridinone derivative. The method comprises the step of removing two methyl groups in Alpha-position of the 2, 6-dimethyl-4-pyridinone derivative under a heating condition by adopting oxygen as an oxidant and ferric chloride anhydrous as a catalyst. The 2, 6-dedimethylation-pyridinone derivative can be simply obtained along with high yield by the processes of cooling, extracting and separating after the reaction. According to the method, the reaction is just carried out in one step, so that the process is simple; the raw materials and the catalyst are the chemistry and chemical raw materials which are low in price and easy to obtain; and the organic solvent in reaction is easily recovered and recycled, so that the whole reaction is a clean and efficient technological process, and the benefit is provided for massive industrial production.

Description

technical field [0001] The present invention relates to the selective removal of 2,6-dimethyl-4-pyridone derivatives of the 2- and 6-methyl method, specifically using oxygen as an oxidant and anhydrous ferric chloride as a catalyst, using DMF is used as a solvent to remove the 2- and 6-methyl groups of 2,6-dimethyl-4-pyridone derivatives. The method has the advantages of environmental friendliness, good compatibility of important functional groups, and good regioselectivity. Background technique [0002] 4-Pyridone derivatives have diverse biological activities and are widely used in chemical and chemical fields such as medicine and pesticides. Their biological activities are mainly reflected in antitumor, antiviral, antibacterial, antiedema, antipsychotic, Met kinase inhibitor, etc. At the same time, they are also a very important class of organic synthesis intermediates. At present, there are a large number of referenced literatures reporting the synthesis methods of py...

Claims

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Application Information

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IPC IPC(8): C07D213/82
Inventor 张志国刘青锋张贵生田庆
Owner HENAN NORMAL UNIV
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