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Preparation of nabumetone

The technology of nabumetone and naphthyl group is applied in the field of preparation of nabumetone, can solve the problems of expensive catalyst, complicated purification method and high production cost, and achieves the effects of low catalyst price, production cost advantage and low cost

Inactive Publication Date: 2007-06-20
ZHEJIANG APELOA JIAYUAN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of this invention is to provide a kind of preparation method of nabumetone, the method prepares intermediate 3-alkoxycarbonyl-4-(6-methoxy-2-naphthyl) by catalytic reduction method in the existing preparation method The butan-2-one step is improved to overcome the expensive catalysts that exist in the prior art, poor selectivity, instability, high production costs and complicated purification methods.

Method used

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  • Preparation of nabumetone

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Dissolve 80g of 6-methoxy-2-naphthaldehyde and 56g of methyl acetoacetate in 350ml of cyclohexane, add 5g of piperidinium phenylacetate, reflux for 5 hours, evaporate the solvent, add 160ml of methanol crystals to the residue, filter, Dry to obtain 110 g of 3-methoxycarbonyl-4-(6-methoxy-2-naphthyl)but-2-en-2-one with a yield of 90%.

[0018] In a 500ml capacity autoclave, add 60g3-methoxycarbonyl-4-(6-methoxy-2-naphthyl)but-2-en-2-one, 6g Raney Ni(W-2), 300ml Methanol, with H 2 Replace the air in the kettle three times, add hydrogen to gauge pressure 1.0Mpa, temperature 40°C, continue hydrogenation, keep the reaction pressure constant, react for 15 hours, TLC detection and tracking until the reaction is complete, filter, add 100ml hydrochloric acid to the filtrate, reflux hydrolysis for 5 hour, cooling, the product was separated out, and the crude product was obtained by filtration, recrystallized from absolute ethanol, filtered, and dried to obtain 42.3 g of white cr...

Embodiment 2

[0020] According to the method described in Example 1, 3-methoxycarbonyl-4-(6-methoxy-2-naphthyl)but-2-en-2-one was prepared. In an autoclave with a capacity of 500ml, add 60g 3-methoxycarbonyl-4-(6-methoxy-2-naphthyl)but-2-en-2-one, 6gRaney Ni(W-2), 280ml methanol, washed with H 2 Replace the air in the kettle three times, add hydrogen to gauge pressure 0.1Mpa, temperature 40°C, continue hydrogenation, keep the reaction pressure constant, react for about 20 hours, TLC detection and tracking until the reaction is complete, filter, add 100ml hydrochloric acid to the filtrate, reflux hydrolysis After cooling for 5 hours, the product was precipitated, and the crude product was obtained by filtration, recrystallized from absolute ethanol, filtered, and dried to obtain 39.5 g of white crystalline powder nabumetone, with a total yield of 81.8% and a GC content ≥ 99%.

Embodiment 3

[0022] According to the method described in Example 1, 3-methoxycarbonyl-4-(6-methoxy-2-naphthyl)but-2-en-2-one was prepared. In an autoclave with a capacity of 500ml, add 60g3-methoxycarbonyl-4-(6-methoxy-2-naphthyl)but-2-en-2-one, 6gRaney Ni(W-2), 150ml butyl acetate and 120ml toluene, use H 2 Replace the air in the kettle three times, add hydrogen until the gauge pressure is 3.0Mpa, and the temperature is 40°C, continue hydrogenation, keep the reaction pressure constant, react for about 8 hours, TLC detection and tracking until the reaction is complete, filter, add 100ml hydrochloric acid to the filtrate, and reflux Hydrolyze for 5 hours, cool, precipitate the product, filter to obtain the crude product, recrystallize from absolute ethanol, filter, and dry to obtain 38.6 g of white crystalline powder nabumetone, the total yield is 80%, and the GC content is more than or equal to 99%.

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Abstract

Production of naphthy-butadiene-meketone is carried out by taking Raney-Ni Wn(n=2-7), Raney Cu or Raney Co as catalysts and catalytic hydrogenating to prepare intermediate 3-carbalkoxy-4-(6-methoxy-2-naphthyl)butyl-2-ketone. It's cheap and simple, and has gentle reactive condition and less corrosion.

Description

technical field [0001] The invention relates to a preparation method of nabumetone. Specifically, it relates to an improved method for preparing intermediate 3-alkoxycarbonyl-4-(6-methoxy-2-naphthyl)butan-2-one by catalytic reduction in the nabumetone synthesis process. Background technique [0002] Nabumetone is also called naprometone, and its chemical name is 4-(6-methoxy-2-naphthyl)-2-butanone. It is a non-steroidal anti-inflammatory drug developed by British Beecham Company. Listed in the early 1980s, it has a good relieving effect on rheumatism and rheumatoid arthritis, which is equivalent to the broad-spectrum anti-inflammatory drug naproxen, and because it does not have a carbonyl group in the molecule, it is irritating to the gastrointestinal tract. It is very small and has been highly evaluated clinically. In recent years, domestic and foreign market demand has increased substantially year after year, and the development prospect is very optimistic. [0003] The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/61C07C49/258
Inventor 王立新李先国雷正兰张拥军伍春林
Owner ZHEJIANG APELOA JIAYUAN PHARMA
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