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Method for synthesizing 5-nitrosalicylaldehyde

A technology of nitrosalicylaldehyde and p-nitrophenol, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problem of polyphosphoric acid viscosity, unfavorable tracking and detection reaction, and difficult 5-nitro Salicylaldehyde industrial production, complex reaction process and other problems, to overcome the difficulty of tracking analysis and detection of reaction process, improve the efficiency of synthesis reaction, the effect of simple post-treatment process

Inactive Publication Date: 2020-09-22
CHANGZHOU VOCATIONAL INST OF ENG
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Problems solved by technology

But the viscosity of polyphosphoric acid is unfavorable for tracking and detection reaction greatly, it is difficult to realize the industrialized production of 5-nitrosalicylaldehyde, and the reaction is violently exothermic in the process of adding hexamethylenetetramine, easy to spray material, and there is a certain degree of uncertainty in the reaction dangerous;
[0008] (3) The Sommelet method is to carry out the esterification reaction between p-nitro-o-cresol and phosphorus oxychloride, and then carry out the free radical-chlorination reaction of the methyl group, and generate cyclohexamethylene tetramine with cyclohexamethylene tetramine. The amine salt is hydrolyzed under the action of acetic acid to generate o-formylphenyl ester, a Sommelet reaction occurs, and finally the target compound is obtained by reflux hydrolysis under strong acidic conditions. The reaction process is complicated and the yield is only 57%.

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  • Method for synthesizing 5-nitrosalicylaldehyde
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Embodiment 1

[0024] The present invention is a kind of method of synthesizing 5-nitro salicylaldehyde (reaction formula sees attached figure 1 ), is to take p-nitrophenol as a raw material, and is prepared by improving Duff reaction and hexamethylenetetramine reaction, comprising the following steps:

[0025] S1: Add hexamethylenetetramine (14g, 0.1mol), p-nitrophenol (14g, 0.1mol) and 13mL trifluoroacetic acid into a four-necked flask, stir, slowly raise the temperature, and add the remaining 17mL of trifluoroacetic acid (30mL in total, 0.4mol), heated to 70°C for reflux reaction for 6 hours to obtain a reaction product mixture;

[0026] S2: After concentrating the reaction product mixture in step S1 to remove part of the trifluoroacetic acid, adding sodium bicarbonate aqueous solution to adjust the pH of the reaction product mixture to about 6, cooling and standing for a period of time, a light yellow solid precipitates, and successively filter, Washing and drying gave 12.1 g of a light...

Embodiment 2

[0029] The present invention is a kind of method of synthesizing 5-nitro salicylaldehyde (reaction formula sees attached figure 1 ), is to take p-nitrophenol as a raw material, and is prepared by improving Duff reaction and hexamethylenetetramine reaction, comprising the following steps:

[0030] S1: Add hexamethylenetetramine (21g, 0.15mol), p-nitrophenol (14g, 0.1mol) and 15mL trifluoroacetic acid into a four-necked flask, stir, slowly raise the temperature, and add the remaining 22.5 mL of trifluoroacetic acid (37.5 mL in total, 0.5 mol) was heated to 78°C for reflux reaction for 7 hours to obtain a reaction product mixture;

[0031] S2: After concentrating the reaction product mixture in step S1 to remove part of the trifluoroacetic acid, adding sodium bicarbonate aqueous solution to adjust the pH of the reaction product mixture to about 6, cooling and standing for a period of time, a light yellow solid precipitates, and successively filter, After washing and drying, 10.6...

Embodiment 3

[0033] The present invention is a kind of method of synthesizing 5-nitro salicylaldehyde (reaction formula sees attached figure 1 ), is to take p-nitrophenol as a raw material, and is prepared by improving Duff reaction and hexamethylenetetramine reaction, comprising the following steps:

[0034] S1: Add hexamethylenetetramine (28g, 0.2mol), p-nitrophenol (14g, 0.1mol) and 13mL trifluoroacetic acid into a four-necked flask, stir, slowly raise the temperature, and add the remaining 17mL of trifluoroacetic acid (30mL in total, 0.4mol), heated to 70°C for reflux reaction for 7 hours to obtain a reaction product mixture;

[0035] S2: After concentrating the reaction product mixture in step S1 to remove part of the trifluoroacetic acid, adding sodium bicarbonate aqueous solution to adjust the pH of the reaction product mixture to about 6, cooling and standing for a period of time, a light yellow solid precipitates, and successively filter, After washing and drying, 11.3 g of a lig...

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Abstract

The invention discloses a method for synthesizing 5-nitrosalicylaldehyde. 5-nitrosalicylaldehyde is prepared by taking p-nitrophenol as a raw material and trifluoroacetic acid as a catalyst through animproved Duff reaction and hexamethylenetetramine reaction. Compared with a salicylaldehyde nitration method, the synthesis method provided by the invention effectively inhibits the generation of isomers in the synthesis process of 5-nitrosalicylaldehyde, and is convenient for separation and purification of a target product; the use of reaction raw materials with high toxicity and serious environmental pollution and high-temperature and high-pressure reaction conditions are avoided, the reaction conditions are mild, the post-treatment process is simple, the synthesis reaction efficiency is improved, and the yield of the 5-nitrosalicylaldehyde reaches 63% or above.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a method for synthesizing 5-nitrosalicylaldehyde. Background technique [0002] 5-nitrosalicylaldehyde, also known as 2-hydroxy-5-nitrobenzaldehyde, is a fine chemical intermediate widely used in the production of medicines, pesticides, dyes and fragrances. [0003] With the acceleration of social progress, people are under more and more pressure, and the number of patients with cardiovascular diseases is also increasing. Therefore, the research of cardiovascular drugs has been paid more and more attention. Dronedarone (dronedaronehydrochloride), the chemical name is 2-n-butyl-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-5-methanesulfonamidobenzofuran, is A polarization inhibitor developed by the French, which is mainly used clinically to treat arrhythmia. [0004] 5-nitrosalicylaldehyde is one of the important raw materials for the synthesis of dro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/44
CPCC07C201/12C07C205/44
Inventor 叶爱英杨利苹张文雯巩冰倩
Owner CHANGZHOU VOCATIONAL INST OF ENG
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