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Synthesis method of 4-hydroxy-8-bromoisoquinoline

A technology of bromoisoquinoline and a synthetic method is applied in the synthesis field of 4-hydroxy-8-bromoisoquinoline, can solve problems such as inability to produce on a large scale, cannot obtain target products, and has a long synthesis route, and achieves strong Effects of schizophrenia, simple synthetic route, and short synthetic route

Active Publication Date: 2016-06-22
SUZHOU KANGRUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The application requires 6 steps of reaction for the prior art, and the synthetic route is long; the total yield is only 15%, and a large amount of inflammable and explosive sodium borohydride is used in the reductive ammonification, so that it cannot be produced on a large scale; Friedel-Crafts reaction temperature requirements are extremely strict, and the reaction must be carried out at -10°C, otherwise the reaction will become complicated, and the target product will not even be obtained. Technical problems, a synthetic method of 4-hydroxy-8-bromoisoquinoline is provided

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Mix o-bromobenzylamine and toluene solution evenly to obtain a toluene solution of o-bromobenzylamine; add p-toluenesulfonic acid and glyoxylic acid to the toluene solution of o-bromobenzylamine, and the o-bromobenzylamine and acetaldehyde The molar ratio of the acid is 1:1, the consumption of p-toluenesulfonic acid is 10% of the quality of o-bromobenzylamine, and the consumption of toluene is 10 times the volume of the quality of o-bromobenzylamine, reflux dehydration under heating conditions, carry out After the oil and water are separated, spin dry directly, and condense to generate the crude product of 2-o-bromophenyliminoacetic acid.

[0023] Add polyphosphoric acid to the crude product of 2-o-bromophenyliminoacetic acid, and stir while heating until the reaction is completed. The heating temperature is 150-170°C. After cooling, pour the mixture obtained from the completion of the fourth step into water and filter it. The filter cake was washed with ether and then ...

Embodiment 2

[0025] 18.6g, 100mmol o-bromobenzylamine and toluene solution are mixed uniformly, and the consumption of toluene is 186ml, and the toluene solution of o-bromobenzylamine is obtained; Add 1.86g p-toluenesulfonic acid and 7.41g, 100mmol glyoxylic acid, the molar ratio of the o-bromobenzylamine and glyoxylic acid is 1:1, the usage of p-toluenesulfonic acid is 10% of the quality of o-bromobenzylamine, reflux under heating Dehydration, oil-water separation, spin-drying directly, and condensation to generate 2-o-bromophenyliminoacetic acid crude product.

[0026] Add 150g of polyphosphoric acid to the crude product of 2-bromophenyliminoacetic acid, and stir while heating until the reaction is completed. The heating temperature is 150-170°C. After cooling, pour the mixture obtained from the completion of the fourth step into water and filter it. , The filter cake was washed with ether and then dried to obtain 17 g of 4-hydroxy-9-bromoisoquinoline with a total yield of 76%.

[0027]...

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PUM

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Abstract

The invention discloses a synthesis method of 4-hydroxy-8-bromoisoquinoline. The method comprises the following steps: mixing bromobenzylamine with a toluene solution, then adding p-toluenesulfonic acid and glyoxylic acid, heating, refluxing, dehydrating and condensing to generate a 2-bromobenzene imidoacetic acid crude product, adding polyphosphoric acid, simultaneously heating and stirring, pouring the product into water for filtering after the reaction is completed, washing filter cake with ethyl ether, then drying the filter cake. According to the synthesis method of 4-hydroxy-8-bromoisoquinoline, bromobenzylamine is used as the raw material; the synthesis route is simple; the process selection is reasonable; the raw material is simple and easily available; the operation and after-treatment are convenient; the total yield reaches up to 76%; the 4-hydroxy-8-bromoisoquinoline is easy to magnify and high in biological activity, can be used as a 5-hydroxytryptamine receptor, and has a strong effect of treating dementia and schizophrenia diseases.

Description

technical field [0001] The application belongs to the technical field of synthesis of pharmaceutical intermediates, and in particular relates to a synthesis method of 4-hydroxyl-8-bromoisoquinoline. Background technique [0002] Isoquinoline compounds are important compounds in organic synthesis and pharmaceutical synthesis, and 4-hydroxy-8-bromoisoquinoline is a typical representative of this type of molecule, which can be synthesized by modifying or derivatizing the functional group of the intermediate A series of novel organic compounds. The latest research shows that these compounds have good biological activity, can act as 5-HT receptors, and have a strong effect on treating dementia and schizophrenia (US2013 / 0317010A1). In recent years, the Suzuki coupling reaction between 4-hydroxy-8-bromoisoquinoline and some aromatic boronic acids has become one of the hotspots in medicinal chemistry to seek some active screening drugs or develop other biological activities. Bec...

Claims

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Application Information

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IPC IPC(8): C07D217/24
CPCC07D217/24
Inventor 徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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