Method of preparing 4-hydroxy-6-decyloxy-7-ethoxy-3-quinoline carboxylic acid ethyl ester

A technology of ethyl quinoline carboxylate and ethoxy, which is applied in a new field of preparation, can solve the problems of harsh reaction conditions and equipment, large waste of intermediate reactions, and large environmental pollution, and meet the requirements of avoiding reaction conditions and equipment Harsh, mild reaction conditions, wide-ranging effects

Inactive Publication Date: 2007-08-08
CHANGSHU OUYAJI BIOMEDICINE INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] About the total synthesis of ethyl 4-hydroxy-6-decyloxy-7-ethoxy-3-quinolinecarboxylate is rarely reported in the literature, only in the British patent (publication number 1469416, the preparation process of quinoline derivatives) Disclosed is a method of introducing amino groups on the benzene ring through diazo coupling, and then cyclization to obtain the product. However, this method uses nitrite and strong acid under long-term low-temperature conditions, and has relatively high requirements for reaction conditions and equipment. Harsh, the intermediate reaction wastes a lot, and it also pollutes the environment; the raw materials used are less commercially available, and the price is expensive, and the post-treatment is more complicated, the yield and product purity are not ideal, so it is not conducive to industrial production

Method used

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  • Method of preparing 4-hydroxy-6-decyloxy-7-ethoxy-3-quinoline carboxylic acid ethyl ester
  • Method of preparing 4-hydroxy-6-decyloxy-7-ethoxy-3-quinoline carboxylic acid ethyl ester
  • Method of preparing 4-hydroxy-6-decyloxy-7-ethoxy-3-quinoline carboxylic acid ethyl ester

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Experimental program
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Effect test

Embodiment 1

[0026] A, the preparation of pyrocatechol diethyl ether (I)

[0027]

[0028] Add catechol (11g, 0.1mol) in the 250ml three-neck flask that reflux condenser, thermometer and magnetic stirring device are housed, 30% sodium hydroxide aqueous solution (20ml, about 0.2mol), ethanol (30ml) and Sodium iodide (0.1g), heat the solution, then slowly drop into the mixture of bromoethane (43.6g, 0.4mol) and ethanol (30ml), keep the oil temperature at 60°C, reflux for 15-18 hours, TLC (thin layer chromatography) showed that the reaction of catechol was complete, let it stand for cooling, separated the upper oil layer, evaporated unreacted bromoethane and solvent ethanol under reduced pressure, and crystallized the remaining oily matter at about 0°C to obtain the crude product . The crude product was recrystallized in ethanol to obtain I (15.0 g), yield 90.3%. The melting point of the product is 42-44°C. In this example, the reason why ethanol is used as the solvent is that the high ...

Embodiment 2

[0049] Other steps are identical with embodiment 1, just the preparation method of the pyrocatechol diethyl ether (I) of A step is as follows:

[0050] Add pyrocatechol (11g, 0.1mol) in the 250ml three-neck flask that reflux condenser, thermometer and magnetic stirring device are housed, 30% sodium hydroxide aqueous solution (50ml, about 0.5mol), ethanol (30ml) and Sodium iodide (0.1g), stirred at room temperature, then slowly added diethyl sulfate (61.6g, 0.4mol) dropwise, kept the oil temperature at 100°C, refluxed for 5-8 hours, TLC (thin layer chromatography) showed that o-phenyl After the reaction of the diphenol is complete, let it stand for cooling, separate the upper oil layer, remove the solvent ethanol under reduced pressure, and crystallize the remaining oil at about 0°C to obtain the crude product. The crude product was recrystallized in ethanol to obtain I (15.7 g), yield 94.5%. The melting point of the product is 42-44°C.

Embodiment 3

[0052] Other steps are identical with embodiment 1, just the preparation method of the pyrocatechol diethyl ether (I) of A step is as follows:

[0053] Add pyrocatechol (11g, 0.1mol) in the 250ml three-neck flask that reflux condenser, thermometer and magnetic stirring device are housed, 15% sodium hydroxide aqueous solution (100ml, about 0.5mol), ethanol (30ml) and Sodium iodide (0.1g), stirred at room temperature, then slowly added diethyl sulfate (61.6g, 0.4mol) dropwise, kept the oil temperature at 100°C, refluxed for 5-8 hours, TLC (thin layer chromatography) showed that o-phenyl After the reaction of the diphenol is complete, let it stand for cooling, separate the upper oil layer, remove the solvent ethanol under reduced pressure, and crystallize the remaining oil at about 0°C to obtain the crude product. The crude product was recrystallized in ethanol to give I (15.3 g), yield 92.1%. The melting point of the product is 42-44°C.

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Abstract

The invention discloses a making method of 4-hydroxy-6-oxy-7-ethoxy-3-quinoline carboxylic acid carbethoxy in the coccidiostat domain, which comprises the following steps: A. preparing catechol diethyl ether; B. making .3, 4-diethyloxy nitrobenzene; C. making 2-ethoxy-4-nitrophenol; D. making 3-ethoxy-4-oxynitrobenzene; E. making 3-ethoxy-4-oxyphenylamine; F. preparing N-methylene ethyl malonate-3-ethoxy-4-oxyphenylamine; G obtaining the product.

Description

Technical field: [0001] The invention relates to a new preparation method of anticoccidiostat, in particular to a preparation method of ethyl 4-hydroxy-6-decyloxy-7-ethoxy-3-quinolinecarboxylate. Background technique: [0002] In the process of raising livestock and poultry, livestock and poultry are easily infected by coccidiosis and cause a series of coccidiosis, which affects the output and quality of the breeding industry. The input of coccidial disease and its treatment has been greatly increased than before, and the veterinary drugs against coccidiosis are also widely used in animal husbandry, such as ethyl 4-hydroxy-6-decyloxy-7-ethoxy-3-quinolinecarboxylate (English Decoquinate / DECOX), the molecular formula is C24H35NO5, and the molecular weight is 417.53. It is about 27 grams and the residual drug concentration in the tissue after 3 days of drug withdrawal is less than 1ppm. Therefore, it has many advantages such as fast drug withdrawal metabolism and less resistan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/56
Inventor 蒋忠良
Owner CHANGSHU OUYAJI BIOMEDICINE INST
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