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Industrial synthesis technique for DL-naproxen

A synthesis process and technology of the process, applied in the field of industrial synthesis process, can solve problems such as low yield, unstable bromide, easy decomposition, etc., and achieve the effect of ensuring operability, saving processing steps and raw materials, and ensuring continuity

Inactive Publication Date: 2008-08-06
江苏八巨药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0041] During the reaction of halogenated compounds in the propionylation process, due to the long time of ketalization and rearrangement, the brominated compounds are unstable, easy to decompose, and the material liquid turns black. It needs to be extracted and decolorized with toluene many times to remove it, so the yield is low. high

Method used

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  • Industrial synthesis technique for DL-naproxen
  • Industrial synthesis technique for DL-naproxen
  • Industrial synthesis technique for DL-naproxen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Put 30g (0.14mol) of propionylnaphthyl ether, 3g of PTS, 20g (0.19mol) of neopentyl glycol into a 500ml three-necked bottle, add 300ml of toluene, install a reflux device with a water separator, and heat up and reflux for 5 to 7 hours , be down to room temperature, add 1% sodium bicarbonate solution 100ml, stir, a large amount of crystals are separated out, filter, filter cake is washed once with 100ml water and 100ml toluene respectively, dry, obtain about 42g (0.14mol) of product I, yield Close to 100%, mp: 131-132°C; content (HPLC) 99.5%.

[0098] Put 30g (0.1mol) of ketal I into a dried 500ml three-necked bottle, add 300ml of dichloroethane, cool down to 10°C, put 38.4g of PTT into the three-necked bottle, and stir for 2 to 5 hours, naturally Warm up to room temperature, add 100ml of water to wash, separate the water layer, then wash with 100ml of 2% aqueous sodium bicarbonate solution, separate the water layer, finally wash with 100ml of water until neutral, dry wi...

Embodiment 2

[0107] Put 30g (0.14mol) of propionylnaphthyl ether, 3g of PTS, 16g (0.21mol) of 1,2-propanediol into a 500ml three-necked bottle, add 300ml of cyclohexane, install a reflux device with a water separator, and heat up and reflux for 10 ~14 hours, be down to room temperature, add 1% sodium bicarbonate solution 100ml, stir, have a large amount of crystals to separate out, filter, filter cake is washed once with 100ml water and 100ml hexanaphthene respectively, dry, obtain about 42g of product I (0.14 mol), the yield is close to 100%, and the content (HPLC) is 99.5%.

[0108] Put 30g (0.1mol) of ketal into a dried 500ml three-necked flask, add 300ml of dichloromethane, cool down to 10°C, put 38.4g of PTT into the three-necked flask, stir for 2 to 5 hours, and naturally heat up to At room temperature, add 100ml of water to wash, separate the water layer, then wash with 100ml of 2% sodium bicarbonate aqueous solution, separate the water layer, finally wash with 100ml of water until ...

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Abstract

The invention relates to an industrial synthesis technique of DL-naproxen, which uses 2-propinonyl-6-methoxynaphthalene is reacted with neopentyl glycol, ethylene alcohol, 1, 3-methyl glycol or 1, 2-methyl glycol via ketol reaction to give ketone I, then processes a-bromo-reaction which is subjected to rearrangement to open ring, at last processes alkali hydrolytic reaction and acidification reaction to obtain DL-naproxen. The industrial synthesis technique of DL-naproxen has simple operation, high yield and low cost, which is fit for commercial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an industrial synthesis process of DL-naproxen. Background technique [0002] DL-body naproxen is an essential pharmaceutical intermediate for the production of naproxen, and naproxen (Naproxen), also known as methoxyisopropionic acid, is a non-steroidal anti-inflammatory analgesic. Its anti-inflammatory, antipyretic, and analgesic effects are good, and the adverse reactions are small. It has been widely used in the world and has become one of the main antipyretic and analgesic drugs and the best-selling over-the-counter drugs in the world. In addition to being recorded in the Chinese Pharmacopoeia, it has also been included in the pharmacopoeias of the United States, Britain, Japan and other countries. According to relevant statistics, non-steroidal anti-inflammatory drugs are currently one of the leading drugs in the world market, with annual sales of about 7 bill...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/64C07C51/00
Inventor 孔立曾运才陈恬
Owner 江苏八巨药业有限公司
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