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Preparation method of 7-methoxy-1-naphthylacetonitrile

A technology of methoxyl and naphthaleneacetonitrile, which is applied in the field of preparation of 7-methoxyl-1-naphthaleneacetonitrile, which can solve the problems of high production cost, high price, and inability to reuse

Inactive Publication Date: 2020-07-07
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] 1) Chinese patents CN201310074356.5 and CN201710463834.X both disclose the synthesis method of 7-methoxy-1-naphthaleneacetonitrile, both of which start with 7-methoxy-3,4-dihydro-1-naphthaleneacetonitrile 7-methoxy-1-naphthalene acetonitrile is obtained by dehydroaromatization of dichlorodicyanobenzoquinone (DDQ) in halogenated hydrocarbons; the by-product of this method is mainly the reduction of DDQ to DDHQ (Dichlorodicyanohydroquinone), serious environmental pollution, poor quality
[0008] 2) Chinese patent CN200510071611.6 discloses a new synthesis method, new crystal form and pharmaceutical composition of agomelatine, which uses 7-methoxy-3,4-dihydro-1-naphthaleneacetonitrile as raw material , using 10% Pd / C and allyl methacrylate in toluene for dehydroaromatization; this method mainly has the high price of Pd / C, which is easy to poison and cannot be reused, resulting in high production costs
[0009] 3) Invention patent WO2014 / 064706, using 7-hydroxy-3,4-dihydro-1-naphthalene acetonitrile as raw material, dehydroaromatization with Pd / C and allyl methacrylate in toluene, after hydroxyl Synthesis of 7-methoxy-1-naphthaleneacetonitrile by methylation; this method also has high Pd / C price, is easy to poison, and cannot be reused, resulting in higher production costs

Method used

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  • Preparation method of 7-methoxy-1-naphthylacetonitrile
  • Preparation method of 7-methoxy-1-naphthylacetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 50.0g (0.25mol) of 7-methoxy-3,4-dihydro-1-naphthaleneacetonitrile and 350ml of toluene into a 500ml four-neck flask, stir to dissolve; add 42.5g (0.34mol) of allyl methacrylate , stirred for 10 minutes; then added 5% ruthenium / carbon 2.5g; heated to 80°C, stirred and reacted for 4hrs; sampling GC analysis: the normalized content of raw materials was 0.5%, and the reaction was completed;

[0030] After the reaction is finished, cool to room temperature, filter with suction, wash with a small amount of toluene, and reuse the catalyst; combine the filtrate and lotion, remove the solvent under reduced pressure until dry, add 300ml of 65% ethanol aqueous solution to the residue, heat to 65°C to dissolve, cool , cooled to 0°C, stirred and crystallized for 1hr; suction filtered, washed with 50% ethanol aqueous solution, and dried to obtain 47.6g of the product 7-methoxy-1-naphthaleneacetonitrile, with a content of 99.3% and a yield of 96.2%; the product was analyzed by NMR...

Embodiment 2～5

[0032] The following examples 2 to 5 are all operated according to the steps of example 1, only the catalyst ruthenium carbon is reused different times, and the implementation results are shown in the following table:

[0033] Embodiment 2~5 experimental result

[0034] Example serial number Ruthenium Carbon Reuse Times Response time (hr) Product content (%) Yield (%) 2 the second time 4.0 99.2 95.1 3 the third time 5.0 99.0 95.4 4 the fourth time 4.0 99.1 96.5 5 the fifth time 5.0 99.4 96.3

Embodiment 6

[0036] Add 50.0g (0.25mol) of 7-methoxy-3,4-dihydro-1-naphthaleneacetonitrile and 350ml of absolute ethanol into a 500ml four-necked flask, stir to dissolve; add 42.5g (0.34 mol), stirred for 10 minutes; then added 5% ruthenium / carbon 2.5g; heated to 70°C, stirred and reacted for 6hrs; sampling GC analysis: the normalized content of raw materials was 0.6%, and the reaction was over;

[0037] After the reaction is finished, cool to room temperature, filter with suction, wash with a small amount of ethanol, and reuse the catalyst; combine the filtrate and lotion, remove the solvent under reduced pressure until dry, add 300ml of 65% ethanol aqueous solution to the residue, heat to 65°C to dissolve, cool, Cool to 0°C, stir and crystallize for 1 hr; filter with suction, wash with 50% aqueous ethanol, and dry the solid to obtain 46.8 g of the product 7-methoxy-1-naphthaleneacetonitrile with a content of 99.5% and a yield of 94.7%.

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Abstract

The invention discloses a preparation method of 7-methoxy-1-naphthylacetonitrile, which is characterized by comprising the following steps of adding 7-methoxy-3, 4-dihydro-1-naphthylacetonitrile intoa first solvent, dissolving, adding allyl methacrylate, uniformly stirring, adding a catalyst ruthenium / carbon, and carrying out dehydrogenation aromatization reaction, and after the reaction is finished, filtering out the catalyst, desolventizing the filtrate under reduced pressure, adding a second solvent, heating to dissolve, cooling, crystallizing, carrying out suction filtration, and drying to obtain the white crystal 7-methoxy-1-naphthylacetonitrile. The preparation method of 7-methoxy-1-naphthylacetonitrile provided by the invention is simple to operate, less in pollution, low in cost,high in yield, less in side reaction and high in product purity, and the catalyst can be repeatedly used.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of 7-methoxy-1-naphthaleneacetonitrile. Background technique [0002] 7-methoxy-1-naphthaleneacetonitrile, the molecular structure is as follows: [0003] [0004] Molecular formula: C 13 h 11 NO; CAS number: 138113-08-3. [0005] 7-methoxy-1-naphthaleneacetonitrile is the key intermediate in the synthesis of agomelatine. Agomelatine, chemically named N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide, is the first melatonin-like antidepressant to be effective in the treatment of Depression, improved sleep parameters and preserved sexual function. It is now on the market in some countries around the world for the treatment of adult patients with depression. [0006] Synthesize 7-methoxyl-1-naphthaleneacetonitrile from 7-methoxyl-3,4-dihydro-1-naphthaleneacetonitrile, mainly contain the following methods: [0007] 1) Chinese patents CN201310074356.5 a...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/37
CPCC07C253/30C07C255/37Y02P20/584
Inventor 沈建伟
Owner SUZHOU JINGYE MEDICINE & CHEM
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