Method for synthesizing 2-methoxy-4-cyano benzaldehyde

A synthesis method, a technology of methyl benzamide, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high price of silver nitrate, unsuitable for industrial production, etc., and achieve easy operation and rapid reaction. , the effect of simple process

Pending Publication Date: 2011-04-20
大连凯飞精细化工有限公司
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Problems solved by technology

[0002] 2-methoxy-4-cyanobenzaldehyde is a very important drug intermediate, so far there is no literature report to synthesize 2-methoxy-4-methylbenzoic acid as raw material The synthetic method of 4-cyanobenzaldehyde
The synthesis of the aldehyde group is also realized by using methyl bromide and then hydrolysis. The hydrolysis reagent of this compound must be a weak base or DMSO (dimethyl sulfoxide), and a strong acid or a strong base will cause the hydrolysis of the cyano group. Document Journal of Medicinal Chemistry, 2007.Vol.50, No.10 report uses silver nitrate to carry out hydrolysis, but silver nitrate price is more expensive, is not suitable for industrialized production

Method used

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  • Method for synthesizing 2-methoxy-4-cyano benzaldehyde
  • Method for synthesizing 2-methoxy-4-cyano benzaldehyde
  • Method for synthesizing 2-methoxy-4-cyano benzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0018] (1) Synthesis of 3-methoxy-4-methylbenzamide: Add 900g (5.42mol) of 3-methoxy-4-methylbenzoic acid into a 2L four-necked reaction flask, add 496ml of thionyl chloride (6.83mol) stirring, began to slowly heat up to 80 ° C, the reaction liquid has a white slurry gradually turned into a brown liquid, and finally turned into a brownish black, about 2h after the reaction is completed, add 150ml of toluene to distill under reduced pressure, and distill off the remaining dichloro sulfoxide. Then the reaction solution is added to the beaker or reaction flask that 2.5L (7.3mol) of 25% ammoniacal liquor is housed, stirs while adding dropwise, there is pale yellow solid to separate out, suction filtration, infrared drying obtains 850g product (2), collects The rate is 95%.

[0019] (2) Synthesis of cyanide: Add 82.5 g (0.5 mol) of amide (2) into the 1L four-necked reaction flask, add 89.3 g (0.75 mol) of thionyl chloride dropwise into the reaction flask, and the dropwise addition...

Embodiment 2

[0023] (1) Synthesis of 3-methoxy-4-methylbenzamide: Add 900g (5.42mol) of 3-methoxy-4-methylbenzoic acid into a 2L four-necked reaction flask, add 496ml of thionyl chloride (6.83mol) stirring, began to slowly heat up to 90 ° C, the reaction liquid has a white slurry gradually turned into a brown liquid, and finally turned into brown black, about 2h after the reaction was completed, add 150ml of toluene to distill under reduced pressure, and distill off the remaining dichloro sulfoxide. The reaction solution is then added to a beaker or a reaction flask with 2.5L (7.3mol) of 25% ammonia, and stirred while adding dropwise, a pale yellow solid is precipitated, filtered by suction, and dried by infrared to obtain 769g of product (2). The rate is 86%.

Embodiment 3

[0025] Reaction (1) is the same with embodiment 1.

[0026] (2) Synthesis of cyanide: Add 82.5 g (0.5 mol) of amide (2) into the 1L four-necked reaction flask, add 89.3 g (0.75 mol) of thionyl chloride dropwise into the reaction flask, and the dropwise addition is completed in about 45 minutes. The temperature was controlled at 80°C, and the reaction was carried out for 0.5h. The reaction solution was poured into 800 g of ice water and stirred while pouring, a yellow solid was precipitated, filtered by suction, and dried to obtain 65 g of product (3), with a yield of 89%.

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Abstract

The invention relates to a method for synthesizing 2-methoxy-4-cyano benzaldehyde which servers as an important medicinal intermediate. The method comprises the following steps: causing 3-methoxy-4-methyl benzoate to react with thionyl chloride react under the heating condition to generate 3-methoxy-4-methyl benzoyl chloride; causing the 3-methoxy-4-methyl benzoyl chloride to react with aqueous ammonia to generate 3-methoxy-4-methyl benzoyl amide; dehydrating the 3-methoxy-4-methyl benzoyl amide to generate 3-methoxy-4-methyl benzonitrile; brominating the 3-methoxy-4-methyl benzonitrile by N-bromosuccinimide (NBS) to generate 3-methoxy-4-benzylene bromide benzonitrile; and hydrolyzing the 3-methoxy-4-benzylene bromide benzonitrile to obtain the target product of 2-methoxy-4-cyano benzaldehyde. The method provided by the invention has the outstanding advantages that the reaction condition is mild, the reactions are rapid, the process is simple, and the operation is easy, thereby being suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic compounds with six-carbon aromatic rings, and relates to the preparation technology of compounds with alkoxy groups, cyano groups and aldehyde groups in benzene rings. Background technique [0002] 2-methoxy-4-cyanobenzaldehyde is a very important drug intermediate, so far there is no literature report to synthesize 2-methoxy-4-methylbenzoic acid as raw material Synthetic method of 4-cyanobenzaldehyde. The preparation method reported in the invention has the advantages of simple operation, high yield and easy industrial production in actual production. The key of the present invention lies in the synthesis of cyano group and aldehyde group on the benzene ring. The synthesis of cyano group on the benzene ring is mostly realized by using cyanide to replace halogen, but cyanide is a highly toxic article. In order to avoid using highly toxic articles, we have adopted The cyano group was efficiently synthesize...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/56C07C253/30
Inventor 马玉慧李珊珊张殿举姜人武王乃伟
Owner 大连凯飞精细化工有限公司
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