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New preparation method of 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

A technology of hydroxybenzoyl group and hydroxybenzoyl chloride is applied in the new preparation field of 2-n-butyl-3--5-nitrobenzofuran, and can solve the problem of no effective solution, complicated production process and high production cost problem, to achieve the effect of low production cost, simplified process flow and low cost

Inactive Publication Date: 2011-09-07
SHANDONG ZOUPING DAZHAN NEW MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the above method involves two-step reactions, the production process is complex, resulting in high production costs and low yields
In the published reports about the preparation method of dronedarone, there is no effective solution to the above problems

Method used

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  • New preparation method of 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
  • New preparation method of 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
  • New preparation method of 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1: Synthesis of 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

[0027] Under nitrogen protection conditions, 44.0 grams of 2-n-butyl-5-nitrobenzofuran and 28.1 grams of 4-hydroxybenzoyl chloride were mixed in 400 milliliters of dichloroethane, 40.1 grams of aluminum trichloride was added, and 30- Stir at 40°C for 12 hours. The reaction solution was added to water, the organic layer was separated, dichloroethane was distilled off, and vacuum-dried to obtain 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran as a light yellow solid of 59.4 g , yield 87.3%. HPLC purity was 98.4%.

Embodiment 2

[0028] Example 2: Synthesis of 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

[0029] Under nitrogen protection conditions, mix 44.0 grams of 2-n-butyl-5-nitrobenzofuran and 28.1 grams of 4-hydroxybenzoyl chloride in 400 milliliters of trichloroethane, add 78.0 grams of tin tetrachloride at room temperature Stir for 12 hours. The reaction solution was added to water, the organic layer was separated, the chloroform was distilled off, and vacuum-dried to obtain 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran as a light yellow solid of 56.0 g, Yield 82.4%. HPLC purity was 97.5%.

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Abstract

The invention belongs to the technical field of a chemical synthesis method, which mainly relates to a preparation method of a dronedarone intermediate 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran. The preparation method of the 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran comprises the following step of: enabling the 2-n-butyl-5-nitrobenzofuran to be subjected to Friedel-Crafts acylation and 4-hydroxybenzoyl chloride reaction to obtain the 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran (compound shown in the formula I). The method has the advantages of simple and convenient processes, low cost and easy acquisition of raw materials, high yield and high safety, and is suitable for industrial production.

Description

technical field [0001] The present invention belongs to the technical field of the preparation method of dronedarone intermediate, in particular to a new preparation method of 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran, such compounds are An important intermediate in the synthesis of the antiarrhythmic drug dronedarone. Background technique [0002] 2-n-Butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran is generally used as an intermediate in the preparation of various products, especially for the final synthesis of aminoalkoxy intermediates of benzoylbenzofuran derivatives, especially the final synthesis of dronedarone (chemical name 2-n-butyl-3-[4-(3-di-n-butylaminopropoxy)benzidine Acyl]-5-methanesulfonamidobenzofuran) and its pharmaceutically acceptable salt intermediates are widely used. [0003] Such aminoalkoxybenzoylbenzofuran derivatives and their pharmaceutically acceptable salts and their therapeutic applications have been disclosed in patent EP 0471609. This c...

Claims

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Application Information

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IPC IPC(8): C07D307/80
Inventor 李岩李丕永林泉生耿磊
Owner SHANDONG ZOUPING DAZHAN NEW MATERIALS
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