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Preparation method for 2-cyano-4'-methylbiphenyl

A technology of sartan biphenyl and p-chlorotoluene, which is applied in the field of preparation of sartan biphenyl, can solve the problems of expensive catalyst, many reaction by-products, and low utilization rate, and achieve simplified post-processing operations and metal catalyst residues , low cost, and the effect of reducing industrial production costs

Inactive Publication Date: 2013-12-25
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this method also has certain shortcomings, such as many reaction by-products, some catalysts are expensive, low utilization rate, difficult recovery, etc.

Method used

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  • Preparation method for 2-cyano-4'-methylbiphenyl
  • Preparation method for 2-cyano-4'-methylbiphenyl
  • Preparation method for 2-cyano-4'-methylbiphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Under nitrogen protection and anhydrous conditions, add 790.6ml of tetrahydrofuran into the fully dried reactor, stir, then add 47.9g of magnesium chips, heat up to 80°C, start to drop 252g of p-chlorotoluene, and control the rate of addition. Keep the temperature at about 80°C, after the dropwise addition is completed, keep the reaction for 5 hours, then cool down to room temperature, and use the Grignard reagent directly for the next reaction.

[0042] Add 790.6ml of tetrahydrofuran, 274g of o-chlorobenzonitrile, 2.52g of nickel iodide, and 2.52g of manganese chloride into the reactor, stir, cool down to -20°C, add one-step Grignard reagent dropwise, and control the temperature at about -20°C. After the dropwise addition, react for 7 hours, add dropwise hydrochloric acid with a mass concentration of 30%, adjust to acidity, and distill off the solvent to obtain the crude product. The obtained crude product is recrystallized with ethyl acetate, and the obtained solid is...

Embodiment 2

[0044] Under nitrogen protection and anhydrous conditions, add 1870ml of diethyl ether into the fully dried reactor, stir, then add 384.0g of magnesium chips, heat up to 30°C, start to drop 504.1g of p-chlorotoluene, and control the rate of addition. Keep the temperature at about 30°C, after the dropwise addition is completed, keep the reaction for 1 hour, then cool down to room temperature, and use the Grignard reagent directly for the next reaction.

[0045] Add 1870ml of diethyl ether, 548.6g of o-chlorobenzonitrile, 126.1g of nickel chloride, 126.1g of manganese sulfate into the reactor, stir, control the temperature to 20°C, add one-step Grignard reagent dropwise, control the temperature at about 20°C, add dropwise After completion of the reaction for 1 h, sulfuric acid with a mass concentration of 30% was added dropwise to adjust to acidity, and the solvent was distilled off to obtain a crude product. The obtained crude product is recrystallized with acetone, and the obt...

Embodiment 3

[0047] Under nitrogen protection and anhydrous conditions, add 5L of toluene to the fully dried reactor, stir, then add 384g of magnesium chips, heat up to 50°C, start to drop 1Kg of p-chlorotoluene, control the rate of addition, and make the temperature Keep it at about 50°C, after the dropwise addition is completed, keep it warm for 3 hours, then cool down to room temperature, and use the Grignard reagent directly for the next reaction.

[0048]Add 5L of toluene, 4.3Kg of o-chlorobenzonitrile, 2.5Kg of nickel sulfate, and 2.5Kg of manganese chloride into the reactor, stir, control the temperature to 0°C, add one-step Grignard reagent dropwise, control the temperature at about 0°C, and add dropwise After completion of the reaction for 3 hours, a mixed acid solution of sulfuric acid and acetic acid with a mass concentration of 30% was added dropwise to adjust to acidity, and the solvent was distilled off to obtain a crude product. The obtained crude product is recrystallized w...

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Abstract

The invention discloses a preparation method for 2-cyano-4'-methylbiphenyl. The invention adopts the following technical scheme: the preparation method comprises the following steps: taking p-chlorotoluene as a raw material for Grignard reaction with magnesium powder in a solvent in the absence of water under nitrogen protection, and coupling a reaction product with chlorobenzonitrile under the catalytic effect of a nickel-manganese composite catalyst to prepare 2-cyano-4'-methylbiphenyl. A Ni (II) / Mn (II) composite catalyst is added into a 2-cyano-4'-methylbiphenyl synthesis reaction system, so that the reaction activity is enhanced and the reaction selectivity is improved; the catalyst is lower in price and easy to recover, so that the postprocessing difficulty is lowered and the production cost is reduced; a recrystallization method is adopted in postprocessing and refining processes, so that the product purity is further improved, a white product is obtained, and the industrialization operation is more convenient.

Description

technical field [0001] The invention relates to the field of catalytic synthesis of pharmaceutical intermediates, in particular to a preparation method of sartan biphenyl. Background technique [0002] Molecular structural formula of sartan biphenyl: [0003] [0004] At present, the drugs with better curative effect on the treatment of hypertension, heart disease, stroke, nephritis and other circulatory system diseases are angiotensin II [referred to as A (II)] antagonist drugs, such as losartan, telmisartan, valsartan, Iprosartan, Irbesartan. And sartan biphenyl (2-cyano-4'-methylbiphenyl, OTBN) is the basic intermediate for the synthesis of these excellent antagonist drugs, which has been widely used in my country's pharmaceutical industry, and it is also the intermediate for the synthesis of liquid crystal materials body. [0005] With the continuous expansion of the domestic antihypertensive sartan drug market, the demand for the drug intermediate - sartan biphenyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07C253/30
Inventor 姜玉钦任保齐侯茜茜毛龙飞张玮玮徐桂清李伟韩会娟
Owner HENAN NORMAL UNIV
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