AU2016102230A4 - Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method - Google Patents
Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method Download PDFInfo
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- AU2016102230A4 AU2016102230A4 AU2016102230A AU2016102230A AU2016102230A4 AU 2016102230 A4 AU2016102230 A4 AU 2016102230A4 AU 2016102230 A AU2016102230 A AU 2016102230A AU 2016102230 A AU2016102230 A AU 2016102230A AU 2016102230 A4 AU2016102230 A4 AU 2016102230A4
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Abstract
Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method, comprising the following steps: equipped with a stirrer, a thermometer, a reaction vessel was added 2.9-3. 1mol 4'-methyl-acetanilide, a certain concentration of 200ml phosphoric acid solution, stirring speed was controlled at 200-260rpm, 0.9mol p-benzoquinone was added in batches, the temperature of the solution is controlled at 60--65 C, the temperature of the solution was dropping naturally during the agitation, there exists solid precipitation after cooling, the temperature of the solution is reduced to 15--19 C, 2L a certain concentration of potassium chloride solution was added, white crystals precipitated, the temperature of the solution was reduce to 11--13 C, filtered, the product was recrystallized from acetone solution with the mass fraction of 90%, and dried in vacuum, ultimately got white granular crystalline 1,2,4-triacetoxy benzene.
Description
Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate
synthesis method TECHNICAL FIELD
The present invention relates to catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method.
BACKGROUND ART
As cataract medications, Catalin prevents the occurrence of cataract development through inhibiting quinones, and it has detoxification for adrenaline antagonistic. It can inhibit the quinones generated by the abnormal metabolism of aromatic amino acid, prevent the formation of insoluble protein crystals, inhibiting the development of cataracts. Its chemical structure is very similar to the insect eye pigment, it has a utility that preventing the water-soluble protein of lens from degenerating, preventing cataract progression. It can prevent the degeneration of the lens as well as the development of cataract disease. 1,2,4-trihydroxybenzene triacetate as catalin drug intermediates, its synthesis method is of great economic significance for improving drug synthesis product quality, reducing the by-product content.
SUMMARY OF THE INVENTION
Object of the present invention is to provide catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method, comprising the following steps: (i) equipped with a stirrer, a thermometer, a reaction vessel was added 2.9-3.lmol 4'-methyl-acetanilide, a certain concentration of 200ml phosphoric acid solution, stirring speed was controlled at 200-260rpm, 0.9mol p-benzoquinone was added in batches, the temperature of the solution is controlled at 60—65 °C, the temperature of the solution was dropping naturally during the agitation, there exists solid precipitation after cooling, the temperature of the solution is reduced to 15—19°C, 2L a certain concentration of potassium chloride solution was added, white crystals precipitated, the temperature of the solution was reduce to 11—13°C, filtered, the product was recrystallized from acetone solution with the mass fraction of 90%, and dried in vacuum, ultimately got white granular crystalline 1,2,4-triacetoxy benzene; wherein, the phosphoric acid solution in step (i) has a mass fraction of 80-95%, the potassium chloride solution in step (i) has a mass fraction of 60—75%.
Throughout the reaction can be summarized as the following reaction formula:
<2) m
Advantage of the present invention is that: reducing the reaction intermediate links, decreasing the reaction temperature and reaction time, improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION
Embodiment 1
Equipped with a stirrer, a thermometer, a reaction vessel was added 2.9mol 4'-methyl-acetanilide, 200ml phosphoric acid solution with a mass fraction of 80%, stirring speed was controlled at 200rpm, 0.9mol p-benzoquinone was added in batches, the temperature of the solution is controlled at 60 °C, the temperature of the solution was dropping naturally during the agitation, there exists solid precipitation after cooling, the temperature of the solution is reduced to 15°C, 2L potassium chloride solution with a mass fraction of 60% was added, white crystals precipitated, the temperature of the solution was reduce to 11 °C, filtered, the product was recrystallized from acetone solution with the mass fraction of 90%, and dried in vacuum, ultimately got white granular crystalline 1,2,4-triacetoxy benzene 192.78g, yield 85%.
Embodiment 2
Equipped with a stirrer, a thermometer, a reaction vessel was added 3.0mol 4'-methyl-acetanilide, 200ml phosphoric acid solution with a mass fraction of 85%, stirring speed was controlled at 230rpm, 0.9mol p-benzoquinone was added in batches, the temperature of the solution is controlled at 62 °C, the temperature of the solution was dropping naturally during the agitation, there exists solid precipitation after cooling, the temperature of the solution is reduced to 17°C, 2L potassium chloride solution with a mass fraction of 70% was added, white crystals precipitated, the temperature of the solution was reduce to 12°C, filtered, the product was recrystallized from acetone solution with the mass fraction of 90%, and dried in vacuum, ultimately got white granular crystalline 1,2,4-triacetoxy benzene 192.32g, yield 87%.
Embodiment 3
Equipped with a stirrer, a thermometer, a reaction vessel was added 3.1 mol 4'-methyl-acetanilide, 200ml phosphoric acid solution with a mass fraction of 95%, stirring speed was controlled at 260rpm, 0.9mol p-benzoquinone was added in batches, the temperature of the solution is controlled at 65 °C, the temperature of the solution was dropping naturally during the agitation, there exists solid precipitation after cooling, the temperature of the solution is reduced to 19°C, 2L potassium chloride solution with a mass fraction of 75% was added, white crystals precipitated, the temperature of the solution was reduce to 13 °C, filtered, the product was recrystallized from acetone solution with the mass fraction of 90%, and dried in vacuum, ultimately got white granular crystalline 1,2,4-triacetoxy benzene 206.39g, yield 91%.
While a number of preferred embodiments have been described, it will be appreciated by persons skilled in the art that numerous variations and/or modifications may be made to the invention without departing from the spirit or scope of the invention as broadly described. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive.
Claims (3)
1. Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method, comprising the following steps :(i) equipped with a stirrer, a thermometer, a reaction vessel was added 2.9-3.1 mol 4'-methyl-acetanilide, a certain concentration of 200ml phosphoric acid solution, stirring speed was controlled at 200-260rpm, 0.9mol p-benzoquinone was added in batches, the temperature of the solution is controlled at 60—65 °C, the temperature of the solution was dropping naturally during the agitation, there exists solid precipitation after cooling, the temperature of the solution is reduced to 15—19°C, 2L a certain concentration of potassium chloride solution was added, white crystals precipitated, the temperature of the solution was reduce to 11—13°C, filtered, the product was recrystallized from acetone solution with the mass fraction of 90%, and dried in vacuum, ultimately got white granular crystalline 1,2,4-triacetoxy benzene.
2. Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method according to claim 1 wherein the phosphoric acid solution in step (i) has a mass fraction of 80-95%.
3. Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method according to claim 1 wherein the potassium chloride solution in step (i) has a mass fraction of 60—75%.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2015109827230 | 2015-12-23 | ||
| CN201510982723.0A CN105503585A (en) | 2015-12-23 | 2015-12-23 | Synthesis method of 1,2,4-triacetoxybenzene serving as catalin drug intermediate |
| CN201610826444X | 2016-09-18 | ||
| CN201610826444.XA CN106431903A (en) | 2015-12-23 | 2016-09-18 | Synthesis method for 1,2,4-triacetoxybenzene serving as Catalin medical intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2016102230A4 true AU2016102230A4 (en) | 2017-02-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016102230A Ceased AU2016102230A4 (en) | 2015-12-23 | 2016-12-23 | Catalin drug intermediates 1,2,4-trihydroxybenzene triacetate synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2016102230A4 (en) |
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2016
- 2016-12-23 AU AU2016102230A patent/AU2016102230A4/en not_active Ceased
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| FGI | Letters patent sealed or granted (innovation patent) | ||
| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |