Production process of 2-amino-3,5-dibromobenzaldehyde

A technology of anthranilaldehyde and its production process, which is applied in the field of medicine and chemical industry, can solve the problems of o-nitrodibromobenzyl not being effectively and rationally utilized, waste of raw materials, and increased cost of waste treatment, so as to realize high-value transformation and promote The effect of reuse

Active Publication Date: 2021-09-28
JIANGXI RONGXING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Yet this method, contains a large amount of o-nitrodibromobenzyl in the production waste, has caused the waste of raw material, and has increased the cost of waste disposal, and o-nitrodibromobenzyl has not been effectively and rationally utilized

Method used

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  • Production process of 2-amino-3,5-dibromobenzaldehyde
  • Production process of 2-amino-3,5-dibromobenzaldehyde
  • Production process of 2-amino-3,5-dibromobenzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0038] In this embodiment 1, o-nitrodibromobenzyl is prepared into o-aminodibromobenzyl extraction reaction solution, comprising the following steps:

[0039] Add 100ml of water, 0.4005mol active iron powder and 0.0097mol hydrochloric acid solution into the reaction flask, stir at room temperature for 30 minutes, add 50g toluene and 0.1695mol o-nitrodibromobenzyl, heat and reflux to HPLC to detect the completion of the o-nitrodibromobenzyl reaction Afterwards (use time 3h), add 5% sodium carbonate aqueous solution to adjust pH=7-9 in the reaction bottle, filter at the temperature of 60-75 ℃ to obtain the filtrate, put the filtrate in the separatory funnel and let it stand for liquid separation. 90.5 g of the o-aminodibromobenzyltoluene reaction solution was obtained, and the purity detected by HPLC was 95%.

Embodiment 2

[0041] In this embodiment 2, o-nitrodibromobenzyl is prepared into o-aminodibromobenzyl extraction reaction solution, comprising the following steps:

[0042] Add 100ml of water, 0.4205mol active iron powder and 0.0097mol hydrochloric acid solution into the reaction flask, stir at room temperature for 30 minutes, add 50g toluene and 0.1695mol o-nitrodibromobenzyl, heat and reflux to HPLC to detect the completion of the o-nitrodibromobenzyl reaction Afterwards (use time 2h), add 5% sodium carbonate aqueous solution to adjust pH=7-9 in the reaction flask, filter at the temperature of 60-75 ℃ to obtain the filtrate, put the filtrate in the separatory funnel and let it stand for liquid separation. 91.5 g of the o-aminodibromobenzyltoluene reaction solution was obtained, and the HPLC detection purity was 96.2%.

Embodiment 3

[0044] In this embodiment 3, o-nitrodibromobenzyl is prepared into o-aminodibromobenzyl extraction reaction liquid, comprising the following steps:

[0045] Add 100ml of water, 0.4205mol of active iron powder and 0.0097mol of hydrochloric acid solution into the reaction flask, stir at 70-80°C for 30 minutes, then cool down to room temperature, add 50g of toluene and 0.1695mol of o-nitrobenzyl bromide, heat and reflux to detect o-nitrobenzyl bromide by HPLC After the reaction of dibromobenzyl bromide is completed (taking 2h), add 5% aqueous sodium carbonate solution to the reaction flask to adjust the pH=7-9, filter at a temperature of 60-75°C to obtain the filtrate, and place the filtrate in a separatory funnel After standing still for liquid separation, 92.1 g of the o-aminodibromobenzyltoluene reaction solution was separated, and the purity detected by HPLC was 96.8%.

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Abstract

The invention relates to the technical field of pharmaceutical chemicals, in particular to a production process of 2-amino-3,5-dibromobenzaldehyde. The method comprises the following steps: mixing iron powder and hydrochloric acid, adding an extracting agent and 3-nitro-o-dibromomethyl benzene, adjusting the pH value to 7-9 after the reaction is finished, conducting filtering, and separating the liquid to obtain an 3-amino-o-dibromomethyl benzene extraction reaction liquid; adding sulfuric acid into the reaction solution, conducting stirring, and conducting separating to obtain a 3-amino-o-dibromomethyl benzene sulfuric acid reaction solution; adding hydrobromic acid into the sulfuric acid reaction solution, dropwise adding bromogen and / or an oxidizing agent, controlling monobromine to be less than or equal to 0.2%, and adding chloroform to obtain a 2-amino-3,5-dibromodibromomethyl benzene organic solution; adding a dimethylamine aqueous solution and sodium bicarbonate into the organic solution, and separating the solution after the reaction to obtain a 2-amino-3,5-dibromobenzaldehyde chloroform reaction solution; and concentrating, refining and decoloring the chloroform reaction solution to obtain the 2-amino-3,5-dibromobenzaldehyde. The method provided by the invention can be used for industrially synthesizing the 2-amino-3,5-dibromobenzaldehyde, and the nitro waste material generated in the o-nitrobenzaldehyde production process can be utilized.

Description

technical field [0001] The application relates to the technical field of medicine and chemical industry, more specifically, it relates to a production process of 3,5-dibromoanthranilic aldehyde. Background technique [0002] 3,5-Dibromo-o-aminobenzaldehyde, also known as 2-amino-3,5-dibromobenzaldehyde, has a molecular weight of 278.93, a melting point of 136-139°C, and a molecular formula of C 7 h 5 Br 2 NO, its structural formula is: [0003] [0004] 3,5-Dibromo-anthranilic aldehyde is a widely used pharmaceutical intermediate, which is widely used in drug synthesis. It is mainly used as an important intermediate for the synthesis of ambroxol hydrochloride, which is one of many A good expectorant new drug approved by the state, with a large market usage and broad prospects. [0005] There are many synthetic pathways for ambroxol hydrochloride reported in the domestic literature, among which the yield is stable, and the route suitable for industrialized mass product...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C223/06
CPCC07C221/00C07C209/365C07C209/74C07C223/06C07C211/52
Inventor 陈学荣吴兴起
Owner JIANGXI RONGXING PHARMA
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