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A method for catalytically synthesizing 5-methyl-3,4-dihydropyridin-2(1h)-one chemical intermediates

A technology of dihydropyridine and methyl is applied in the field where methyl 3-methyl-2-cyclobutyrate is used as a raw material, and can solve the problems of difficulty in meeting environmental protection requirements, difficulty in recovering morpholine, etc., and achieves low production cost, Good catalytic effect, easy to recycle and apply

Active Publication Date: 2019-09-27
JIANGSU YANGNONG CHEM GROUP +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problem of this process is that a large amount of high-salt wastewater is generated during the acidolysis of cyclobutane, and it is difficult to recover morpholine in industrial production, which is difficult to meet the requirements of environmental protection.

Method used

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  • A method for catalytically synthesizing 5-methyl-3,4-dihydropyridin-2(1h)-one chemical intermediates
  • A method for catalytically synthesizing 5-methyl-3,4-dihydropyridin-2(1h)-one chemical intermediates
  • A method for catalytically synthesizing 5-methyl-3,4-dihydropyridin-2(1h)-one chemical intermediates

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 340.41g of cyclobutane (content 80.37%), 872.85g of 15% ammonia water (the molar ratio of ammonia water to cyclobutane is 6:1) and 10.21g of iron powder (the amount of catalyst is 3% of the amount of cyclobutyl) Into a 2L autoclave, control the stirring speed to 400r / min, and keep the reaction at 60°C for 3h. Subsequently, the obtained reaction kettle liquid was subjected to suction filtration, and the filter cake was washed several times with a small amount of 155.47 g of water to obtain 25.38 g of wet catalyst and 1365.15 g of filtrate. Then the filtrate was distilled under normal pressure to recover 1031.85 g of ammonia water with a concentration of 9.78%, and 192.43 g of morpholine was recovered through negative pressure distillation with a concentration of 49.16%. Finally, the still material was distilled under high vacuum to obtain 134.51 g of crude pyridone, with a content of 74.24%. The crude pyridone was recrystallized from chlorobenzene and dried to obtai...

Embodiment 2-5

[0027] On the basis of Example 1, ammoniacal liquors of different concentrations were adopted (the number of moles was constant), and other conditions were constant. The obtained results are shown in Table 1.

[0028] The impact of the different ammonia concentrations of table 1 on the product yield

[0029] Example number Ammonia concentration / % Pyridone Yield / % Example 2 5 60.14 Example 3 10 63.87 Example 4 20 64.51 Example 5 25 62.95

Embodiment 6-10

[0031] On the basis of Example 1, different catalyst systems were used, and other conditions remained unchanged. The obtained results are shown in Table 2.

[0032] The impact of different catalyst systems on the product yield in table 2

[0033]

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Abstract

The invention belongs to the technical field of organic chemical industry and relates to a method for catalytic synthesis of a 5-methyl-3,4-dihydropyridin-2 (1H)-one chemical intermediate. More particularly, the invention relates to pyridine prepared from 3-methyl-2-(4-morpholinyl)methyl cyclobutyrate through catalysis and ammonolysis, and the yield of pyridine is not lower than 80%. According to the method for synthesizing pyridone from cyclobutyl substances through catalysis and ammonolysis, salt-containing wastewater is not produced, and morpholine is easy to recycle; and the method has the advantages of simple process route, high product yield, simplicity and easiness in recycle and use of the catalyst and the like, is applicable to industrial production and has wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and relates to a method for synthesizing chemical intermediates of 5-methyl-3,4-dihydropyridine-2(1H)-one (abbreviation: pyridone, CAS number: 91936-25-3), More specifically, it relates to a 3-methyl-2-(4-morpholinyl)cyclobutanoic acid methyl ester (abbreviation: cyclobutane, CAS No.: 91936-24-2) as raw material, through catalytic ammonolysis Synthesize pyridone with a yield not lower than 80%. The present invention has the advantages of simple process route, cheap catalyst and easy recovery, less industrial waste water, high product yield and the like. Background technique [0002] Pyridone, whose structure is shown in formula (1), is an important chemical intermediate, which can generate 2-chloro-5-picoline and 2,3-dichloro-5-picoline after chlorination , both of which are very important pesticide and pharmaceutical intermediates. Among them, 2-chloro-5-picoline can be used...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/86
Inventor 王根林丁克鸿徐林王刚殷恒志崔竞方王铖陆林华
Owner JIANGSU YANGNONG CHEM GROUP
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