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A kind of preparation method of 4-methylaminoantipyrine
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A technology of aminoantipyrine and antipyrine, which is applied in the new synthesis field of 4-methylaminoantipyrine, can solve the problems of many types and large quantities of impurities, and achieve high product purity, easy-to-obtain raw materials, easy-to-use effects
Inactive Publication Date: 2019-08-27
ZHEJIANG HAISEN PHARMACY CO LTD
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Problems solved by technology
In the various intermediates of Analgin and crude products of Analgin produced according to the current production process, there are many types and large quantities of impurities
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Embodiment 1
[0018] Add 2 g (10 mmol) of aminoantipyrine, 10 g of 1-methyl-3-butylimidazolium tetrafluoroborate ionic liquid, and macroporous weakly basic styrene-based anion exchange resin Styrene-DVB into a 100 mL three-neck flask (D301 R) 0.2g, dimethyl carbonate 0.9g (10 mmol), react at 160°C for 5 hours, extract 3×30mL with toluene, concentrate, column chromatography Petroleum ether: ethyl acetate (volume ratio) = 5 : 1 mixed solvent was used as a developing solvent for separation and purification to obtain 1.93 g of the product with a yield of 89%.
[0021] Add 2 g (10 mmol) of aminoantipyrine, 30 g of 1-methyl-3-butylimidazolium tetrafluoroborate ionic liquid, and macroporous weakly basic styrene-based anion exchange resin Styrene-DVB into a 100 mL three-neck flask (D301 R) 0.6g, dimethyl carbonate 13.5g (15 mmol), react at 120°C for 10 hours, extract 3×30mL with toluene, concentrate, column chromatography petroleum ether: ethyl acetate (volume ratio) = 5 : 1 mixed solvent was used as a developing solvent for separation and purification to obtain 1.89 g of the product with a yield of 87%.
Embodiment 3
[0023] Add 2 g (10 mmol) of aminoantipyrine, 20 g of 1-methyl-3-butylimidazolium tetrafluoroborate ionic liquid, and macroporous weakly basic styrene-based anion exchange resin Styrene-DVB into a 100 mL three-neck flask (D301 T) 0.6g, dimethyl carbonate 1.0g (11 mmol), react at 180°C for 15 hours, extract 3×30mL with toluene, concentrate, column chromatography Petroleum ether: ethyl acetate (volume ratio) = 5 : 1 mixed solvent was used as a developing solvent for separation and purification to obtain 1.93 g of the product with a yield of 89%.
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Abstract
The invention discloses a preparation method of 4-methylaminoantipyrine. The preparation method consists of: taking aminoantipyrene shown as formula (I) as the raw material, in a 1-methyl-3-butylimidazolium tetrafluoroborate ionic liquid reaction medium, and under the action of solid alkali, carrying out dimethyl carbonate methylation one-step reaction to obtain 4-methylaminoantipyrine shown as formula (II). The reaction equation is shown as the specification, and the solid alkali is macroporous weakly basic styrene type anion exchange resin. The technology has the characteristics of easy operation and high product purity, is a new synthetic technical route, and has the advantages of safety and easily available raw materials, thus being conducive to industrial production.
Description
technical field [0001] The invention relates to a pharmaceutical intermediate, specifically a new synthesis method of 4-methylaminoantipyrine. Background technique [0002] 4-Methylaminoantipyrine (MAA for short), also named 1,2-dihydro-1,5-dimethyl-4-(methylamino)-2-phenyl-3H -Pyrazol-3-one, the English name is 1,2-Dihydro-1,5-DiMethyl-4-(methylamino)-2-phenyl-3H-pyrazol-3-one. This compound is an important raw material of many antipyretic and analgesic drugs, and is most commonly used as an intermediate of antipyretic and analgesic and non-steroidal anti-inflammatory analgesic drugs Analgin. At present, there are not many reports on the synthesis of 4-methylaminoantipyrine in the literature since 1974. The method for industrially synthesizing 4-methylaminoantipyrine is to start from aminoantipyrine and use methyl formate Acylation to generate 4-(formylamino)antipyrine, then methylate with dimethyl sulfate under alkaline conditions to obtain 4-formylmethylaminoantipyrine,...
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