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Preparation method of 5-amino-2,4,6-triiodo-1,3-phthalic acid impurity

A technology of phthalic acid and amino, applied in the field of preparation of impurity 5-amino-2,4-diiodo-1,3-benzenedicarboxylic acid, can solve the problems of no preparation method, difficult separation, difficult separation and purification, etc. Achieve the effects of simple operation, high yield and purity, and simple post-treatment

Active Publication Date: 2021-05-11
ZHEJIANG STARRY PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

5-amino-2,4-diiodo-1,3-benzenedicarboxylic acid, as the key reaction intermediate of 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid, was Identified as an impurity, but there is no clear quality standard for the detection and analysis of 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid at home and abroad
[0009] The main reasons are the following two points: first of all, there is no literature report on the exclusive synthesis of 5-amino-2,4-diiodo-1,3-benzenedicarboxylic acid at home and abroad so far, and there is no preparation method for reference, which increases the preparation time. Difficulty; furthermore, it is difficult to separate, if it is separated and purified from the reaction mother liquor, it will be difficult to separate and purify due to problems such as solubility and separation

Method used

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  • Preparation method of 5-amino-2,4,6-triiodo-1,3-phthalic acid impurity
  • Preparation method of 5-amino-2,4,6-triiodo-1,3-phthalic acid impurity
  • Preparation method of 5-amino-2,4,6-triiodo-1,3-phthalic acid impurity

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Experimental program
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Effect test

Embodiment 1

[0046] Embodiment 1: Add 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid (50g, 89.5mmol) and deionized water (300mL) in a clean reaction flask equipped with a mechanical stirrer, Start stirring to make the mixture uniform, cool the reaction system to 5-10°C, add sodium hydroxide (7.2g, 170.9mmol) in batches to make 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid Completely dissolve and maintain the reaction system at 5-10°C, add palladium carbon (10%) (0.25g, 0.5w%) after the dissolution is clarified. Cool the reaction system to 1-5°C, dropwise add sodium borohydride (3.4g, 89.5mmol) alkali solution (dissolve 3.6g sodium hydroxide in 100mL deionized water, cool to room temperature and add sodium borohydride to dissolve), and maintain the system The temperature is 1-5°C, add dropwise for 0.5h, and continue to react at 1-5°C for 4.5h after the dropwise addition is completed. After the reaction is over, filter the reaction solution under reduced pressure to separate pallad...

Embodiment 2

[0047] Embodiment 2: Add 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid (50g, 89.5mmol) and deionized water (300mL) in a clean reaction flask equipped with a mechanical stirrer, Start stirring to make the mixture uniform, cool the reaction system to 5-10°C, and add potassium hydroxide (10.7g, 170.9mmol, purity ≥ 90%) in batches to make 5-amino-2,4,6-triiodo-1, The 3-phthalic acid was completely dissolved and the reaction system was maintained at 5-10°C. Palladium carbon (10%) (0.25g, 0.5w%) was added after the dissolution was clarified. Cool the reaction system to 1-5°C, dropwise add sodium borohydride (3.4g, 89.5mmol) alkali solution (dissolve 5.4g potassium hydroxide in 100mL deionized water, cool to room temperature and add sodium borohydride to dissolve), and maintain the system The temperature is 1-5°C, add dropwise for 0.5h, and continue to react at 1-5°C for 4.5h after the dropwise addition is completed. After the reaction is over, filter the reaction solution unde...

Embodiment 3

[0048] Embodiment 3: Add 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid (50g, 89.5mmol) and deionized water (300mL) in a clean reaction flask equipped with a mechanical stirrer, Start stirring to make the mixture uniform, cool the reaction system to 5-10°C, add sodium hydroxide (7.2g, 170.9mmol) in batches to make 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid Completely dissolve and maintain the reaction system at 5-10°C, add palladium carbon (10%) (0.25g, 0.5w%) after the dissolution is clarified. Cool the reaction system to 1-5°C, dropwise add potassium borohydride (4.8g, 89.5mmol) alkali solution (dissolve 3.6g sodium hydroxide in 100mL deionized water, cool to room temperature and add potassium borohydride to dissolve), and maintain the system The temperature is 1-5°C, add dropwise for 0.5h, and continue to react at 1-5°C for 4.5h after the dropwise addition is completed. After the reaction is over, filter the reaction solution under reduced pressure to separate ...

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Abstract

The invention relates to a preparation method of 5-amino-2,4,6-triiodo-1,3-phthalic acid impurity component, namely 5-amino-2,4-diiodo-1,3-phthalic acid as shown in a formula (1). Through preparation of the 5-amino-2,4,6-triiodo-1,3-phthalic acid impurity, a standard substance is provided for qualitative and quantitative analysis of the 5-amino-2,4,6-triiodo-1,3-phthalic acid impurity, so the product quality of 5-amino-2,4,6-triiodo-1,3-phthalic acid is improved, and the method has important guiding significance on guaranteeing the quality of a non-ionic iodine contrast agent with 5-amino-2,4,6-triiodo-1,3-phthalic acid as a mother ring structure. The invention provides the method for rapidly and efficiently preparing 5-amino-2,4-diiodo-1,3-phthalic acid, and a blank in a related synthesis field is filled.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and more specifically relates to an impurity 5-amino-2,4-diiodo in the preparation process of 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid - The preparation method of 1,3-phthalic acid. Background technique [0002] Since Wilhelm C. Roentgen accidentally discovered X-ray imaging in 1895, X-ray radiographic technology has gradually evolved into the basis of contemporary medical imaging. Despite the explosive growth in the use of ultrasound and magnetic resonance imaging (MRI) in medical diagnosis over the past few decades, X-rays are still used in 75-80% of all imaging diagnoses, Especially CT-enhanced imaging, and X-ray contrast agents play a vital role in such diagnosis. [0003] With the in-depth study of X-ray contrast agents, it is found that elements with high atomic numbers can be used as contrast enhancing agents. In 1924, sodium iodide as the first water-soluble contrast agent ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/62C07C227/16C07C227/42
CPCC07C229/62C07C227/16C07C227/42
Inventor 骆栋平沈伟艺何小兵年四昀潘建满孙学超
Owner ZHEJIANG STARRY PHARMA