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7-methoxy naphthyl acetonitrile synthesis method

A technology of methoxynaphthalene acetonitrile and methoxyl group, applied in the field of synthesizing 7-methoxynaphthalene acetonitrile, can solve the problems of high cost, expensive metal palladium, and high product cost, achieve low cost, less sewage treatment, and reduced difficulty Effect

Inactive Publication Date: 2017-03-29
SUZHOU HOMESUN PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But used a large amount of noble metal palladium and allyl acrylate in this prior art, because metal palladium is very expensive, product cost is higher, and toxic allyl acrylate also brings pollution to environment
[0007] Chinese Journal of Pharmaceutical Industry 2008, 39 (3) pp 161-163 has reported the method that dehydroaromatization becomes 7-methoxynaphthalene acetonitrile with DDQ, this method has used stoichiometric DDQ, not only cost is higher, and because The DDQ reduction product turns black, and a large amount of black reduction product in the reaction solution makes the post-treatment impossible to extract and stratify, which increases the difficulty of post-reaction treatment. At the same time, a large amount of black wastewater also increases the pressure on environmental protection

Method used

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Experimental program
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Effect test

Embodiment 1

[0025] Add 100 milliliters of dichloromethane, 10 grams (0.05 moles) of 7-methoxy-3,4-dihydronaphthalene acetonitrile, 1.15 grams of DDQ (0.005 moles) in a 250 milliliter pressure cooker, and feed oxygen at a pressure of 2 kPa, Stir the reaction at room temperature for about 6 hours, the reaction does not absorb further 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 ethanol- Water (volume ratio) 50:50 was recrystallized to obtain 9.4 g of the product 7-methoxynaphthaleneacetonitrile with a purity of 99.2% and a yield of 95%. The product was analyzed by NMR, and the hydrogen spectrum 1HNMR (CDCl3): 3.95 (s, 3H), 4.05 (s, 2H), 7.06 (d, 1H), 7.20~7.81 (m, 5H).

Embodiment 2

[0027] Add 150 milliliters of dichloromethane, 19.9 grams (0.1 moles) of 7-methoxy-3,4-dihydronaphthalene acetonitrile, 1.15 grams of DDQ (0.005 moles) in a 500 milliliter pressure cooker, and feed oxygen at a pressure of 2 kPa, Stir the reaction at room temperature for about 6 hours, the reaction does not absorb further oxygen, the reaction is stopped, 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 ethanol- Water (volume ratio) 40:60 was recrystallized to obtain 17.7 g of the product 7-methoxynaphthaleneacetonitrile with a purity of 98.5% and a yield of 90%.

Embodiment 3

[0029] Add 200 ml of dichloroethane, 19.9 g (0.1 mol) of 7-methoxy-3,4-dihydronaphthalene acetonitrile, 2.3 g of DDQ (0.01 mol) in a 500 ml 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 further absorb oxygen, and the reaction stops. The reaction solution is poured into 100 ml of saturated sodium bicarbonate solution for washing, and the organic layer is washed with 100 ml of water. - Recrystallization from water (volume ratio) 60:40 to obtain 17.5 g of the product 7-methoxynaphthaleneacetonitrile with a purity of 98% and a yield of 89%.

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Abstract

The invention discloses a 7-methoxy naphthylacetonitrile synthesis method, which comprises: 1) using 7-methoxy-3,4-dihydro naphthylacetonitrile as a raw material, adopting DDQ as a catalyst, carrying out an oxidation reaction on the 7-methoxy-3,4-dihydro naphthylacetonitrile and introduced oxygen in a halogenated alkane solvent to obtain 7-methoxy naphthylacetonitrile; and 2) extracting the reaction liquid obtained in the step 1), washing, concentrating, and re-crystallizing to obtain the 7-methoxy naphthylacetonitrile. According to the present invention, the 7-methoxy naphthylacetonitrile synthesis method has advantages of low cost, convenient post-treatment and less post-treatment sewage, wherein the by-product is water so as to provide the advantage of green environmental protection.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular 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] A synthetic route of agomeladin is as follows: [0004] [0005] Among them, the compound (B) 7-methoxynaphthaleneacetonitrile is an important i...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/54
CPCC07C253/30C07C255/54
Inventor 樊超
Owner SUZHOU HOMESUN PHARMA
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