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Method for preparing decoquinate intermediate 2-oxethyl-4-nitrophenol potassium

A technology of diethoxynitrobenzene and potassium nitrophenolate, which is applied in the preparation of the intermediate 2-ethoxy-4-nitrophenolate of the anticoccidial drug decoquinate, the intermediate of decoquinate In the field of preparation, it can solve the problems of low cost, long reaction time, waste of raw materials, etc., and achieve the effects of mild reaction conditions, reduced reaction time, and simple process

Active Publication Date: 2013-02-06
QILU ANIMAL HEALTH PROD +1
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Problems solved by technology

This scheme has the problems of long reaction cycle and low yield
Especially the synthesis of the intermediate 2-ethoxy-4-nitrophenolate potassium needs to be reacted in a high temperature environment for a long time, the average synthesis cycle is about 20-24 hours, and the yield can only reach 60-67%
It causes a great waste of raw materials, and the reaction cycle is too long, which increases the cost
[0005] The problem that above-mentioned technique exists is mainly reflected in the process of preparing intermediate 2-ethoxyl-4-nitrophenate potassium, so as long as a kind of intermediate 2-ethoxyl-4-nitrophenolate with high yield and low cost can be provided The preparation method of potassium nitrophenate can solve the preparation problem of ethyl 4-hydroxyl-6-decyloxyl-7-ethoxyl-3-quinolinecarboxylate

Method used

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  • Method for preparing decoquinate intermediate 2-oxethyl-4-nitrophenol potassium
  • Method for preparing decoquinate intermediate 2-oxethyl-4-nitrophenol potassium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A kind of preparation method of decoquinate intermediate 2-ethoxy-4-nitrophenate potassium, the steps are as follows:

[0033] Add 36g of 3,4-diethoxynitrobenzene, 32.6g of potassium hydroxide, 300ml of ethylene glycol, and benzyltributylammonium chloride into a 1000ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirring device 0.72g, under the condition of reaction temperature of 110°C, stir and reflux for 10h, monitor the reaction in liquid phase to complete the reaction, cool down to 0-5°C to crystallize, let the crystal grow for 3 hours, filter, and wash the precipitate twice with ethyl acetate , 100ml each time, dried at 80°C to obtain 33.6g of potassium 2-ethoxy-4-nitrophenate, with a molar yield of 89.1%;

[0034] According to the structure confirmation of nuclear magnetic spectrum, the obtained product is potassium 2-ethoxy-4-nitrophenolate. The NMR results are as figure 1 Shown as: 1 H-NMR (CDCl 3 )δ7.74(d,1H,Ar-H),7.50...

Embodiment 2

[0036] A kind of preparation method of decoquinate intermediate 2-ethoxy-4-nitrophenate potassium, the steps are as follows:

[0037] Add 42.2g of 3,4-diethoxynitrobenzene, 38.2g of potassium hydroxide, 57.3ml of water, 352ml of ethylene glycol monoethyl ether and benzyl Tributyl ammonium chloride 3.4g, at the reaction temperature of 108°C, stirred and refluxed for 10h, the liquid phase monitored the reaction was completed, cooled to 0-5°C to crystallize, stood for 3 hours to grow crystals, filtered, and precipitated Wash twice with ethyl acetate, 100ml each time, and dry at 80°C to obtain 39.8g of potassium 2-ethoxy-4-nitrophenolate, with a molar yield of 90.0%;

[0038] According to the structure confirmation of nuclear magnetic spectrum, the obtained product is potassium 2-ethoxy-4-nitrophenolate. The NMR results are: 1 H-NMR (CDCl 3 )δ7.74(d,1H,Ar-H),7.50(s,1H,Ar-H),6.38(d,1H,Ar-H),3.94(q,2H,-OCH 2 CH 3 ),1.29(t,3H,-OCH 2 CH 3 ).

Embodiment 3

[0040] A kind of preparation method of decoquinate intermediate 2-ethoxy-4-nitrophenate potassium, the steps are as follows:

[0041] Add 36g of 3,4-diethoxynitrobenzene, 32.6g of potassium hydroxide, 293.4ml of water, 300ml of ethylene glycol dimethyl ether and benzyl Tributyl ammonium chloride 3.6g, under the condition of reaction temperature of 80°C, stirred and refluxed for 10h, the liquid phase monitored the completion of the reaction, cooled to 0-5°C to crystallize, stood for 3 hours to grow crystals, filtered, and precipitated Wash twice with ethyl acetate, 100ml each time, and dry at 80°C to obtain 33.4g of potassium 2-ethoxy-4-nitrophenolate, with a molar yield of 88.5%;

[0042] According to the structure confirmation of nuclear magnetic spectrum, the obtained product is potassium 2-ethoxy-4-nitrophenolate. The NMR results are: 1 H-NMR (CDCl 3 )δ7.74(d,1H,Ar-H),7.50(s,1H,Ar-H),6.38(d,1H,Ar-H),3.94(q,2H,-OCH 2 CH 3),1.29(t,3H,-OCH 2 CH 3 ).

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Abstract

The invention relates to a method for preparing a decoquinate intermediate. The method includes the following steps of adding 3, 4-diethoxynitrobenzene, a potassium hydroxide solution with concentration of 10% to 50% (wt / wt), a solvent and a catalyst in a reactor, stirring to perform reflux reaction for 10 hours at the reaction temperature of 80 DEG C to 130 DEG C, cooling to 0 DEG C to 5 DEG C to crystallize, still standing and crystal growing for 2 to 4 hours, filtering, and drying to obtain 2-oxethyl-4-nitrophenol potassium. The method has the advantages that benzyltributylammonium chloride is utilized as the catalyst, the reaction time is greatly shortened, the reaction condition is mild, the process is simple, the operation is easy, and simultaneously the yield of products is substantially improved.

Description

technical field [0001] The invention relates to a preparation method of a decoquinate intermediate, in particular to a preparation method of an anticoccidial drug decoquinate intermediate 2-ethoxy-4-nitrophenate potassium, belonging to the technical field of veterinary drug preparation . Background technique [0002] Coccidiosis is a parasitic disease that causes severe losses in poultry meat and egg production. The multiplication of parasites in the small intestine leads to prevent damage, which reduces feed intake and absorption of nutrients in the feed. Coccidiosis is a parasitic disease caused by the single-celled parasite Eimeria (Eimeria), and its incidence generally leads to a mortality rate of more than 20%. With the gradual increase in the number of poultry breeding, coccidiosis has become a serious threat to the production and quality of the breeding industry. In recent years, the investment in the treatment of coccidiosis in the global animal husbandry has incre...

Claims

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Application Information

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IPC IPC(8): C07C205/37C07C201/12
Inventor 肖阳刘全才孔梅吴连勇
Owner QILU ANIMAL HEALTH PROD
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