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Method for synthesizing 7-methoxynaphthalene acetonitrile

A technology of methoxynaphthalene acetonitrile and methoxy, 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 post-treatment sewage, low cost, and low application cost Effect

Inactive Publication Date: 2017-11-24
TAICANG HONGSHAN ENVIRONMENTAL PROTECTION TECH CO LTD
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  • 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-methoxynaphthalene acetonitrile 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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Examples

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Effect test

Embodiment 1

[0024] Such as figure 2 Shown is the method for synthesizing 7-methoxynaphthaleneacetonitrile. 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

[0026] Such as figure 2 Shown is the method for synthesizing 7-methoxynaphthaleneacetonitrile. 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

[0028] Such as figure 2 Shown is the method for synthesizing 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 7-methoxynaphthalene acetonitrile. An intermediate 7-methoxynaphthalene acetonitrile is obtained by carrying out an oxidation reaction of 7-methoxy-3,4-naphthalene acetonitrile serving as a raw material, dichloro-dicyano-benzoquinone serving as a catalyst and oxygen in a halogenated hydrocarbon solvent. The method is simple, low in production cost, high in reaction overall yield, high in product quality, environmentally friendly and convenient in industrialized production, and has great popularization significance.

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. 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 prior art, such as figure 1 As shown, a synthetic route of agomelatine (C) disclosed in European Patent EP1564...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/37
CPCC07C253/30C07C255/37
Inventor 刘露
Owner TAICANG HONGSHAN ENVIRONMENTAL PROTECTION TECH CO LTD
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