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5-nitro-1,2,3-benzene tricarboxylic acid synthesizing method

A technology of trimellitic acid and nitro group, applied in the field of pharmaceutical chemical intermediate: 5-nitro-1, can solve the problems of high reaction temperature, complicated post-processing, long time and the like, and achieve high reaction yield and high product purity , the effect of simple operation

Inactive Publication Date: 2009-02-04
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has a higher reaction temperature and a longer time; excessive potassium nitrate in the reaction will produce a lot of potassium salt, which makes the aftertreatment complicated and pollutes the equipment; the salt produced after the reaction is removed with a large amount of water, which brings serious waste water pollution; The three hydrophilic groups contained in the product molecule make the product have a certain solubility in water, which reduces the yield and purity, and is not suitable for large-scale production
At present, there is no manufacturer that can produce 5-nitro-1,2,3-benzenetricarboxylic acid on a large scale

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0020] Add 90 g of fuming sulfuric acid into a 250 mL three-necked flask, and continue to add 60 g of fuming nitric acid and 30 g of 1,2,3-benzenetricarboxylic acid while stirring. The temperature was raised slowly, and the reaction was carried out at 50-80°C for 12 hours. After the reaction was complete, the temperature was lowered to 10°C, kept at this temperature for 5 hours, and suction filtered. The filtrate reclaims, after thick product is washed twice with sherwood oil, dry, obtain light yellow granular solid 13.0g, yield is 35.7%, HPLC purity is 97.8%, Shimadzu LC-10A, (select C18 post (4.6mm * 250mm , 5 μm) chromatographic columns; Mobile phase is 30% (v / v) aqueous methanol (gradient elution); analysis time 20min; detection wavelength is 254nm) data are shown in Table 1:

[0021] Table 1

[0022] peak number

[0023] 9

Embodiment 2

[0025] Add 180 g of fuming sulfuric acid into a 500 ml three-necked flask, and continue to add 120 g of fuming nitric acid and 30 g of 1,2,3-benzenetricarboxylic acid under stirring. The temperature rises slowly, and the reaction is carried out at 80-100°C for 24 hours. After the reaction was complete, the temperature was lowered to 10° C., kept at this temperature for 9 hours, and suction filtered. The filtrate was recovered, the crude product was washed twice with ethyl acetate, and then dried to obtain 22.0 g of a light yellow granular solid with a yield of 60.4% and an HPLC purity of 98.3%.

Embodiment 3

[0027] Add 150 g of fuming sulfuric acid into a 500 ml three-necked flask, and continue to add 80 g of fuming nitric acid and 30 g of 1,2,3-benzenetricarboxylic acid under stirring. The temperature was raised slowly, and the reaction was carried out at 100-130° C. for 12 hours. After the reaction was complete, the temperature was lowered to 10°C, kept at this temperature for 5 hours, and suction filtered. The filtrate was recovered, the crude product was washed twice with acetone, and then dried to obtain 28.2 g of a light yellow granular solid with a yield of 77.5% and an HPLC purity of 98.6%.

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Abstract

The invention provides a synthetic method of a pharmaceutical and chemical intermediate 5-nitro-1, 2, 3-benzene tricarboxylic acid and includes the following steps: when oleum and fuming nitric acid are provided, by taking the 1, 2, 3-benzene tricarboxylic acid shown by formula (II) as the raw material, the nitrating reaction is carried out for 5 to 24 hours under the temperature of 50 to 150 DEG C; after the reaction is over, the 5-nitro-1, 2, 3-benzene tricarboxylic acid is obtained by the post-treatment of the reaction solutions; the method is high in yield ratio and the product is high in purity and the operation is simple; the reaction filtrates can be recycled; the organic solvents in the post-treatment can be recovered and are suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing a pharmaceutical chemical intermediate: 5-nitro-1,2,3-benzenetricarboxylic acid. (2) Background technology [0002] 5-nitro-1,2,3-benzenetricarboxylic acid, structural formula sees formula (I), is a kind of intermediate that is applied to synthetic medicine, and it can be obtained through nitration reaction by 1,2,3-benzenetricarboxylic acid, specifically The method is: in the nitration system of concentrated sulfuric acid and potassium nitrate, after 18 hours under the condition of 135-140 ° C, the final product 5-nitro-1, 2, 3-benzenetricarboxylic acid is obtained, and the yield is 50% (US4245120 ). The method has a higher reaction temperature and a longer time; excessive potassium nitrate in the reaction will produce a lot of potassium salt, which makes the aftertreatment complicated and pollutes the equipment; the salt produced after the reaction is removed with a large amount of water, which ...

Claims

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Application Information

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IPC IPC(8): C07C205/57C07C201/08
Inventor 潘建林陈维华喻彪
Owner HANGZHOU NORMAL UNIVERSITY
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