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Method for synthesizing agomelatine important intermediate 7-methoxy naphthylacetonitrile

A technology of methoxynaphthalene acetonitrile and agomelatine, which is applied in the field of organic compound synthesis, can solve the problems of increasing environmental protection pressure, inability to extract and stratify, expensive metal palladium, etc., and achieve less sewage treatment, low cost and high product quality stable effect

Inactive Publication Date: 2017-09-15
TAICANG DATANG CHEM FIBER FACTORY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, a large amount of precious metal palladium and allyl acrylate are used in this patented technology, because metal palladium is very expensive, resulting in higher product costs
[0004] In addition, if figure 1 Shown, Chinese Journal of Pharmaceutical Industry 2008, 39 (3) pp 161-163 has reported the method that dehydroaromatization becomes 7-methoxynaphthaleneacetonitrile with dichlorodicyanobenzoquinone (DDQ), this method uses Stoichiometric DDQ not only has a high cost, but also because the DDQ reduction product turns black, a large amount of black reduction product in the reaction solution can not be extracted and separated after treatment, and a large amount of black wastewater also increases the pressure on environmental protection

Method used

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  • Method for synthesizing agomelatine important intermediate 7-methoxy naphthylacetonitrile

Examples

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Effect test

Embodiment 1

[0025] Such as figure 2 The method for synthesizing the important intermediate of agomelatine, 7-methoxynaphthaleneacetonitrile, is shown. Add 150 ml of dichloromethane, 19.9 g (0.1 mol) of 7-methoxy-3,4-dihydronaphthalene acetonitrile, 1.15 g of DDQ (0.005 mol) in a 500 ml pressure cooker, and feed oxygen at a pressure of 2 kPa at room temperature Under stirring reaction for about 5 hours, the reaction does not further absorb oxygen, the reaction stops, the reaction solution is poured into 100 ml of saturated sodium bicarbonate solution for washing, the organic layer is washed with 100 ml of water, the organic layer is concentrated, and the residue is washed with 50 ml of ethanol- Water=4:1 recrystallized to obtain 18.3 g of the product 7-methoxynaphthaleneacetonitrile with a purity of 98.5% and a yield of 93%.

Embodiment 2

[0027] Such as figure 2 The method for synthesizing the important intermediate of agomelatine, 7-methoxynaphthaleneacetonitrile, is shown. Add 200 milliliters of ethylene dichloride, 19.9 grams (0.1 moles) of 7-methoxy-3,4-dihydronaphthalene acetonitrile, 2.3 grams of DDQ (0.01 moles) in a 500 milliliter pressure cooker, and feed oxygen at a pressure of 3 kPa, Stir the reaction at room temperature for about 4 hours, the reaction does not absorb further oxygen, the reaction stops, the reaction solution is poured into 100 ml of saturated sodium bicarbonate solution for washing, the organic layer is washed with 100 ml of water, the organic layer is concentrated, and the residue is washed with 60 ml of ethanol -Water=5:1 recrystallization, the product 7-methoxynaphthalene acetonitrile 17.5 g, purity 98%, yield 89%.

Embodiment 3

[0029] Such as figure 2 Shown is the method for synthesizing the important intermediate of agomelatine, 7-methoxynaphthaleneacetonitrile. Add 100 ml of dichloromethane, 10 g (0.05 mol) of 7-methoxy-3,4-dihydronaphthalene acetonitrile, 2.3 g of DDQ (0.01 mol) in a 250 ml pressure cooker, and feed oxygen at a pressure of 1 kPa at room temperature Under stirring reaction for about 6 hours, the reaction does not further absorb oxygen, the reaction stops, the reaction solution is poured into 50 ml of saturated sodium bicarbonate solution for washing, the organic layer is washed with 50 ml of water, the organic layer is concentrated, and the residue is washed with 30 ml of ethanol- Water=4:1 recrystallized to obtain 9 grams of product 7-methoxynaphthaleneacetonitrile with a purity of 98.2% and a yield of 91%.

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Abstract

The invention provides a method for synthesizing an agomelatine important intermediate 7-methoxy naphthylacetonitrile. According to the invention, 7-methoxy-3,4-naphthalene acetonitrile is taken as a raw material, 2,3-dicyano-5,6-dichlorobenzoquinone is taken as a catalyst, and the materials are subjected to an oxidation reaction with oxygen in a halogenated hydrocarbon solvent to obtain the intermediate 7-methoxy naphthylacetonitrile. The method is concise, the production cost is low, the integral yield of the reaction is high, product quality is good, environmental protection is realized, the method is convenient for industrial production, and has large popularization meaning.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a method for synthesizing 7-methoxynaphthaleneacetonitrile, an important intermediate of agomelatine. Background technique [0002] Agomelatine, as the first antidepressant of melatonin structural analogue, is currently approved by the European Union for the treatment of adult depression. It is a new type of antidepressant and is a melatonin receptor agonist and 5 - T2 receptor antagonists, which are active in the central nervous system, are mainly used for the treatment of melatonin system diseases, and also for sleep disorders, that is, to regulate the sleep-wake cycle, which can adjust the sleep structure of patients at night and improve sleep. In the treatment of patients with severe depressive disorders, agomelatine has shown good clinical application effect. [0003] In the existing technology, such as figure 1 As shown, a synthetic route of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/37
CPCC07C253/30C07C255/37
Inventor 刘惠峰
Owner TAICANG DATANG CHEM FIBER FACTORY
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