4-formaldoxime benzoate derivative preparation method

A technology of oximobenzoic acid and cyanobenzoic acid is applied in the directions of oxime preparation, organic chemistry and the like, can solve the problems of high production raw material cost, harsh reaction conditions, increase industrial cost and the like, and achieves low production cost, short synthesis route, The effect of high product yield

Active Publication Date: 2017-05-10
荆门医药工业技术研究院 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since the active hydrogen reducing agent is introduced in the first step of the reaction, it generally needs to be used in a low temperature environment, the reaction conditions are harsh, and the industrial cost is increased. At the same time, there is a certain safety in a large amount of active hydrogen reducing agent and its post-treatment Hidden dangers lead to complex post-reaction treatment, so there are disadvantages such as high production raw material costs, more product impurities and low yields

Method used

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  • 4-formaldoxime benzoate derivative preparation method
  • 4-formaldoxime benzoate derivative preparation method
  • 4-formaldoxime benzoate derivative preparation method

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Experimental program
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Embodiment 1

[0019] The synthetic route of one of the 4-formaldoximobenzoate derivatives (methyl 2-methyl-4-formaldoximobenzoate):

[0020]

[0021] Preparation of methyl 2-methyl-4-formaldoximobenzoate: Add 20 ml of methanol to dissolve methyl 2-methyl-4-cyanobenzoate (2.86 g), then add 1.15 g of hydroxylamine hydrochloride and 1.73 g anhydrous sodium carbonate, finally add 20 ml distilled water, at 70 o C was refluxed for 8 hours, cooled to room temperature, and concentrated under reduced pressure to obtain a crude product. The crude product was recrystallized with a mixed solvent of ethyl acetate and petroleum ether to obtain the pure target product, methyl 2-methyl-4-formaldoximobenzoate (2.53 g), with a yield of 87%. The appearance of the product is white crystal, the content is 99.2% (HPLC). [Mobile phase: water: methanol (5:2); detection wavelength: 240 nm; flow rate: 1ml / min; solution preparation: take 0.01g sample and dilute it to 25 ml with mobile phase; injection volume 5 ...

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Abstract

The invention provides a 4-formaldoxime benzoate derivative preparation method. The method mainly includes steps: dissolving 4-cyanobenzoate derivatives and hydroxylamine hydrochloride into an alcohol solvent, adding an appropriate amount of alkali, and performing reflux reaction to obtain a target product 4-formaldoxime benzoate derivative. According to the method, cyano compounds are adopted to directly obtain oxime compounds through one-step reaction. The method has advantages of mild reaction conditions, simplicity in operation, low cost, high product yield, high purity and the like and is suitable for large-scale production.

Description

technical field [0001] The invention relates to the technical field of organic synthetic chemistry, in particular to a method for preparing 4-formaldoxime benzoate derivatives in one step from 4-cyanobenzoate derivatives. Background technique [0002] Oxime compounds are a class of compounds with carbon-nitrogen double bonds (-C=N-). This type of compound can not only use nitrogen and oxygen atoms to coordinate with guest molecules to become redox probe molecules, but also the current The design, synthesis and biological activity research is one of the hotspots in medicinal chemistry research. Oxime compounds are easy to prepare and relatively stable, and can be used for the protection of aldehydes and ketones, the activation of α-positions, the purification of aldehydes and ketones, the identification of carbonyl compounds, the preparation of amines and amides, and the synthesis of amides, amines, nitriles, and isoxazoles Important intermediates of phenoline, isoquinolin...

Claims

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Application Information

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IPC IPC(8): C07C249/04C07C251/48
CPCC07C249/04C07C251/48
Inventor 王勇李立威黄道友
Owner 荆门医药工业技术研究院
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