CN101210013A - Lewis acid catalysis aminolysis method for synthesizing piroxicam - Google Patents
Lewis acid catalysis aminolysis method for synthesizing piroxicam Download PDFInfo
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- CN101210013A CN101210013A CNA2006101613770A CN200610161377A CN101210013A CN 101210013 A CN101210013 A CN 101210013A CN A2006101613770 A CNA2006101613770 A CN A2006101613770A CN 200610161377 A CN200610161377 A CN 200610161377A CN 101210013 A CN101210013 A CN 101210013A
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- lewis acid
- piroxicam
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- compound
- synthesizing
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Abstract
The invention discloses a synthetic method for piroxicam which mainly relates to a compound (I) is catalyzed in silicate lewis, reaction time of a direct ammonolysis method is 4 times shorter (about 4-5h) than the reaction time of a, and the ammonolysis is complete. b the yield of the ammonolysis is high and is more than or equal to 85 percent and does not have decomposes and carbonization; meanwhile, resultant of the invention can be purified easily, thereby the synthetic method for the piroxicam is suitable for scale production.
Description
Technical field
The present invention relates to a kind of synthetic method of piroxicam.
Background technology
Piroxicam is the common drug of treatment of arthritis, and the main synthetic method of factory is at present: a, soluble saccharin and chloracetate condensation;
B, condenses are under the organic bases condition, and ring expansion methylates simultaneously;
C, first thing and 2-aminopyridine alkylbenzene mutually in, carry out ammonia and separate, reaction finishes, crystallisation by cooling.
This technology subject matter is: in the step c technology, generally at 130～140 ℃, the reaction times is at 28～35h for the ammonolysis reaction temperature.The subject matter of this method is that the reaction times is longer, and raw material and product under 130～140 ℃ high temperature, the decomposition and the carbonization of part take place for a long time, cause product yield lower, usually 60～70%, product color is relatively poor, outward appearance is pale brown look, is difficult to decolouring and removes.
Summary of the invention
Purpose of the present invention is sought an energy and is finished the technology that first thing ammonia is separated within a short period of time, reduces the decomposition of raw material and product, improves ammonia and separates yield, improves the visual appearance of product.
Concrete implementation step: see 1
Preferred exemplifying embodiment:
In the glassed steel reaction vessels of 2000L, add first ethyl ester thing 140Kg, dimethylbenzene 1500L, silica gel 10Kg.Be warming up to 100 ℃ of amino pyrrole 52Kg of adding 2-, continue to be warming up to the solvent refluxing temperature, keep refluxing slowly, steam the ethanol of reaction generation and the mixture of dimethylbenzene simultaneously, TLC follows the tracks of reaction, and reaction in 4.5-5 hour finishes.Underpressure distillation, the control temperature in the kettle is no more than 70 ℃, when the system volume be about cumulative volume 1/3 the time stop distillation, be cooled to normal temperature, stir 6-8h and filter, be i.e. crude product.
Crude product adds methyl alcohol 1500L and adds the 15Kg gac, refluxes 30 minutes, filters, and is cooled to normal temperature, stirs 6-8h, methyl alcohol drip washing, 60-70 ℃ is dried by the fire 3-5h, measure product 140.5Kg, yield 85%.Press Cp2005 version standard detection, outward appearance; Off-white color, content 〉=99%.
Methanol mother liquor reclaims methyl alcohol to overall 1/3 o'clock, and cooling stirring at normal temperature 6-8h filters and collects product, oven dry measure product 10Kg, yield 5.7%, this product meet the Cp2005 version and require to add up to yield.Add up to yield 90.7%.
Claims (2)
1. method by lewis acid catalysis aminolysis synthesizing piroxicam
It is characterized in that comprising following step successively:
A, according to a certain percentage in alkyl benzene solvent, add compound (I), lewis acid catalyst, 2-aminopyridine;
B, be warming up to backflow, steam the mixture of alcohol/alkylbenzene simultaneously, the 4～5h in reaction times finishes;
C, be cooled under 10～15 ℃ of the normal temperature, crystallization 6～8h filters;
D, filter cake recrystallizing methanol, decolorizing with activated carbon.
2. according to described in the claim 1a
A, solvent are often referred to boiling point at the alkyl aromatic kind solvent more than 130 ℃, and as dimethylbenzene, isopropyl benzene etc., the weight ratio of solvent and compound (I) is advisable with 10～15 between 5～20.
B, lewis acid catalyst are often referred to the silicates material, as silica gel, heteropolyacid, cover holder soil etc., and consumption is usually in 0.05～0.1 of compound (I) weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006101613770A CN101210013A (en) | 2006-12-25 | 2006-12-25 | Lewis acid catalysis aminolysis method for synthesizing piroxicam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006101613770A CN101210013A (en) | 2006-12-25 | 2006-12-25 | Lewis acid catalysis aminolysis method for synthesizing piroxicam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101210013A true CN101210013A (en) | 2008-07-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006101613770A Pending CN101210013A (en) | 2006-12-25 | 2006-12-25 | Lewis acid catalysis aminolysis method for synthesizing piroxicam |
Country Status (1)
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| CN (1) | CN101210013A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101665472B (en) * | 2009-06-15 | 2011-08-24 | 威海迪素制药有限公司 | Preparation method of 2-methyl-3. 4-dihydro-4-oxo-2H-1. 2-benzothiazine-3-carboxylic ethyl ester-1, 1-dioxide |
-
2006
- 2006-12-25 CN CNA2006101613770A patent/CN101210013A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101665472B (en) * | 2009-06-15 | 2011-08-24 | 威海迪素制药有限公司 | Preparation method of 2-methyl-3. 4-dihydro-4-oxo-2H-1. 2-benzothiazine-3-carboxylic ethyl ester-1, 1-dioxide |
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| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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Open date: 20080702 |