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Method for preparing 3-butyl-4-benzyloxy-aniline

A technology of benzyloxyaniline and butyryl nitrobenzene is applied in the field of preparation of intermediates and can solve problems such as high cost, unsatisfactory yield and product purity, harsh conditions and the like

Inactive Publication Date: 2012-07-04
ZHEJIANG GENEBEST PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In comparison, trimethoprimate (Methylbenzoquat, methylbenzoquinate, benzquinate) has better drug efficacy, and the biggest feature is that it has no drug resistance, so the market price is relatively low. the most expensive
[0005] After consulting a large number of domestic and foreign related documents and patents, we proposed a synthetic route with independent intellectual property rights to synthesize the key intermediate 3-butyl-4-benzyloxyaniline. Improved, the Italian patent (publication number 1320189) discloses a method of reducing butyryl by hydrazine hydrate to obtain the corresponding intermediate, but the reaction conditions of this method require high temperature, reaching 190 ° C, the energy consumption is very large, and the conditions are harsh , the post-processing is more complicated, and the yield and product purity are not ideal, so it is not conducive to industrial production

Method used

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  • Method for preparing 3-butyl-4-benzyloxy-aniline
  • Method for preparing 3-butyl-4-benzyloxy-aniline

Examples

Experimental program
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Effect test

Embodiment 1

[0021] A. Preparation of 3-benzyloxy-4-butyrylnitrobenzene

[0022] Add 2-butyryl-5-nitrophenol (20.9 g, 0.1 mol), DMF (N, N-di Methylformamide, 200g) and sodium carbonate (12.7g, about 0.12mol), stirred evenly and heated to 60°C, then slowly added benzyl chloride (14.0g, about 0.11mol) dropwise, and kept the reaction mixture after the dropwise addition The temperature was 60-70°C and the stirring reaction was continued for 4 hours, then ice water was added to precipitate a solid, which was collected by filtration and dried to obtain 3-benzyloxy-4-butyrylnitrobenzene (27.6g) with a yield of 92.3%.

[0023] B. Preparation of 1-(2-benzyloxy-4-nitrophenyl)-1-butanol

[0024] In a 500ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirring device, add 3-benzyloxy-4-butyrylnitrobenzene (29.9, 0.1mol), and the weight ratio concentration is 95% ethanol (300g ), after stirring evenly, add sodium borohydride (3.8g, 0.1mol) in batches, control the ...

Embodiment 2

[0031] Other steps are identical with embodiment 1, just the preparation method of the 3-benzyloxy-4-butyrylnitrobenzene of A step is as follows:

[0032] Add 2-butyryl-5-nitrophenol (20.9 g, 0.1 mol), DMF (N, N-di Methylformamide, 42g) and sodium carbonate (11.8g, about 0.11mol), stirred evenly and heated to 65°C, then slowly added benzyl chloride (12.8g, about 0.1mol) dropwise, and kept the reaction mixture after the dropwise addition The temperature was 60-70°C and the stirring reaction was continued for 4 hours, then ice water was added to precipitate a solid, which was collected by filtration and dried to obtain 3-benzyloxy-4-butyrylnitrobenzene (25.9g) with a yield of 86.6%.

Embodiment 3

[0034] Other steps are identical with embodiment 1, just the preparation method of the 3-benzyloxy-4-butyrylnitrobenzene of A step is as follows:

[0035]Add 2-butyryl-5-nitrophenol (20.9 g, 0.1 mol), DMF (N, N-di Methylformamide, 150g) and potassium carbonate (17.9g, about 0.13mol), after stirring evenly, the temperature was raised to 60°C, and then benzyl chloride (14.0g, about 0.11mol) was slowly added dropwise, and the reaction mixture was kept The temperature was 60-70°C and the stirring reaction was continued for 4 hours, then ice water was added to precipitate a solid, which was collected by filtration and dried to obtain 3-benzyloxy-4-butyrylnitrobenzene (27.4g) with a yield of 91.6%.

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Abstract

A method for preparing 3-butyl-4-benzyloxy-aniline, relates to a a method for preparing 3-butyl-4-benzyloxy-aniline that is a crucial intermediate of broad-spectrum anticoccidial pesticide nequinate. The method includes following steps in turns: using 2-butyryl-5-nitro-phenol as raw materials, proceeding substitution reaction with benzyl chloride, reduction reaction with sodium borohydride or potassium borohydride, chlorination reaction with thionyl chloride in turns, at last proceeding hydrogenation at presence of catalyst to obtain 3-butyl-4-benzyloxy-aniline. The invention provides a novelsynthetic route, reaction condition of each step is mild, the process is simple and every reaction is common operation, which can avoid strict reaction condition of high-temperature and high-pressureeffectively.

Description

technical field [0001] The invention relates to a method for preparing an intermediate of an anticoccidial drug trimethoprim, in particular to a method for preparing 3-butyl-4-benzyloxyaniline. Background technique [0002] In the process of raising livestock and poultry, livestock and poultry are easily infected by coccidia and cause a series of diseases, which affect the yield and quality of the breeding industry. The input of anti-parasitic veterinary drugs is also widely used in animal husbandry, and quinoline anticoccidiostats are an important raw material of veterinary drugs. Since there are mainly quinoline rings in its molecular structure, it is possible to form different types of anticoccidial raw materials by replacing them with different substituents. Among them, there are mainly butyl hydroxyquinoline (Byqyuni late butyl quinoline), ethoquinoline (Decoquinate decoquinate, decanoquinate, decoquinate), trimethoprim (Methylbenzoquatate, methyl benzoquinoate, benzo...

Claims

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Application Information

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IPC IPC(8): C07C217/86C07C213/02
Inventor 宋苗根
Owner ZHEJIANG GENEBEST PHARMA
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