AU2016102238A4 - Talosalate drug intermediates 2-acetoxyl group benzoic acid-3-hydroxy benzene phthalic ester synthesis method - Google Patents
Talosalate drug intermediates 2-acetoxyl group benzoic acid-3-hydroxy benzene phthalic ester synthesis method Download PDFInfo
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- AU2016102238A4 AU2016102238A4 AU2016102238A AU2016102238A AU2016102238A4 AU 2016102238 A4 AU2016102238 A4 AU 2016102238A4 AU 2016102238 A AU2016102238 A AU 2016102238A AU 2016102238 A AU2016102238 A AU 2016102238A AU 2016102238 A4 AU2016102238 A4 AU 2016102238A4
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- benzoic acid
- acetoxyl group
- phthalic ester
- talosalate
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Abstract
Talosalate drug intermediates 2 - acetoxyl group benzoic acid - 3 hydroxy benzene phthalic ester synthesis method , comprising the following steps: equipped with a stiffer and a reflux condenser, the reaction vessel was added 0.24 mol acetylsalicylic acid (2), 0.24-0.27mol 3-amine phthalide (3), 30- 40ml isopropanol solution, 230-260ml cyclohexane solution, controlling the stirring speed 130-160rpm, reflux 4-6h, atmospheric pressure distillation of cyclohexane, and vacuum distillation distilled solid, solid was washed with brine solution, filtration, recrystallized from ethyl acetate solution, got white solid 2 - acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester.
Description
Talosalate drug intermediates 2-acetoxyl group benzoic acid-3-hydroxy benzene phthalic ester synthesis method
TECHNICAL FIELD
The present invention relates to talosalate drug intermediates 2 -acetoxyl group benzoic acid-3-hydroxy benzene phthalic ester synthesis method.
BACKGROUND ART
Talosalate is antipyretic, analgesic, as well as the majority of anti-inflammatory, anti-rheumatic effects. It can inhibit prostaglandin synthesis, and can also inhibit the release of inflammatory process, bradykinin change lymphocyte response, reducing migration and phagocytosis of granulocytes and monocytes. It is because of NSAID inhibits prostaglandin synthesis, in addition to analgesic and anti-inflammatory effects, but also at the same time a corresponding side effects. 2 - acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester as talosalate 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 talosalate drug intermediates 2 - acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester synthesis method, comprising the following steps: (i) equipped with a stirrer and a reflux condenser, the reaction vessel was added 0.24 mol acetylsalicylic acid (2), 0.24-0.27mol 3- amine phthalide (3), 30- 40ml isopropanol solution, 230-260ml cyclohexane solution, controlling the stirring speed 130-160rpm, reflux 4-6h, atmospheric pressure distillation of cyclohexane, and vacuum distillation distilled solid, solid was washed with brine solution, filtration, recrystallized from ethyl acetate solution, got white solid 2 - acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester (1); wherein isopropanol solution in step (i) has a mass fraction of 65-70%, cyclohexane solution in step (i) has a mass fraction of 45-50%, vacuum distillation in step (i) has a pressure of 1.8-1.9kPa, brine solution in step (i) is any one of sodium sulfate solution or potassium nitrate solution; ethyl acetate solution in step (i) has a mass fraction of 85-90%.
The throughout reaction process can be summarized using the following reaction formula:
Advantage of the present invention is that: the reaction intermediate links are reduced, reducing the reaction temperature and reaction time, improving the reaction yield. DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION Embodiment 1
Equipped with a stirrer and a reflux condenser, the reaction vessel was added 0.24 mol acetylsalicylic acid (2), 0.24mol 3- amine phthalide (3), 30 ml isopropanol solution with a mass fraction of 65%, 230 ml cyclohexane solution with a mass fraction of 45% , controlling the stirring speed 130 rpm, reflux 4 h, atmospheric pressure distillation of cyclohexane, and vacuum distillation in a pressure of 1.8 kPa distilled solid, solid was washed with sodium sulfate solution, filtration, recrystallized from ethyl acetate solution with a mass fraction of 85%, got white solid 2 - acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester 60.65 g, yield 81%.
Embodiment 2
Equipped with a stirrer and a reflux condenser, the reaction vessel was added 0.24 mol acetylsalicylic acid (2), 0.26mol 3- amine phthalide (3), 35 ml isopropanol solution with a mass fraction of 65%, 240 ml cyclohexane solution with a mass fraction of 45% , controlling the stirring speed 140 rpm, reflux 5 h, atmospheric pressure distillation of cyclohexane, and vacuum distillation in a pressure of 1.85 kPa distilled solid, solid was washed with potassium nitrate, filtration, recrystallized from ethyl acetate solution with a mass fraction of 87%, got white solid 2 - acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester 63.65 g, yield 85%.
Embodiment 3
Equipped with a stirrer and a reflux condenser, the reaction vessel was added 0.24 mol acetylsalicylic acid (2), 0.27mol 3- amine phthalide (3), 40 ml isopropanol solution with a mass fraction of 70%, 260 ml cyclohexane solution with a mass fraction of 50% , controlling the stirring speed 160 rpm, reflux 6 h, atmospheric pressure distillation of cyclohexane, and vacuum distillation in a pressure of 1.9 kPa distilled solid, solid was washed with sodium sulfate solution, filtration, recrystallized from ethyl acetate solution with a mass fraction of 90%, got white solid 2 - acetoxyl group benzoic acid-3-hydroxy benzene phthalic ester 66.64 g, yield 89%.
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 (4)
1. Talosalate drug intermediates 2-acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester synthesis method, comprising the following steps: (i) equipped with a stirrer and a reflux condenser, the reaction vessel was added 0.24 mol acetylsalicylic acid (2), 0.24-0.27mol 3- amine phthalide (3), 30-40ml isopropanol solution, 230-260ml cyclohexane solution, controlling the stirring speed 130-160rpm, reflux 4-6h, atmospheric pressure distillation of cyclohexane, and vacuum distillation distilled solid, solid was washed with brine solution, filtration, recrystallized from ethyl acetate solution, got white solid 2 - acetoxyl group benzoic acid - 3 - hydroxy benzene phthalic ester (1); wherein isopropanol solution in step (i) has a mass fraction of 65-70%, cyclohexane solution in step (i) has a mass fraction of 45-50%.
2. Talosalate drug intermediates 2 - acetoxyl group benzoic acid - 3 -hydroxy benzene phthalic ester synthesis method according to claim 1 wherein vacuum distillation in step (i) has a pressure of 1.8-1.9kPa.
3. Talosalate drug intermediates 2 - acetoxyl group benzoic acid - 3 -hydroxy benzene phthalic ester synthesis method according to claim 1 wherein brine solution in step (i) is any one of sodium sulfate solution or potassium nitrate solution.
4. Talosalate drug intermediates 2 - acetoxyl group benzoic acid - 3 -hydroxy benzene phthalic ester synthesis method according to claim 1 wherein ethyl acetate solution in step (i) has a mass fraction of 85-90%.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2015109827796 | 2015-12-24 | ||
CN201510982779.6A CN105503799A (en) | 2015-12-24 | 2015-12-24 | Synthesis method of talosalate drug intermediate 2-acetoxybenzoic acid-3-hydroxyphthalide ester |
CN201610814183.XA CN106397378A (en) | 2015-12-24 | 2016-09-11 | Synthetic method of talosalate drug intermediate 2-acetoxybenzoic acid-3-hydroxyphthalide ester |
CN201610814183X | 2016-09-11 |
Publications (1)
Publication Number | Publication Date |
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AU2016102238A4 true AU2016102238A4 (en) | 2017-02-16 |
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Application Number | Title | Priority Date | Filing Date |
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AU2016102238A Ceased AU2016102238A4 (en) | 2015-12-24 | 2016-12-23 | Talosalate drug intermediates 2-acetoxyl group benzoic acid-3-hydroxy benzene phthalic ester synthesis method |
Country Status (1)
Country | Link |
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AU (1) | AU2016102238A4 (en) |
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2016
- 2016-12-23 AU AU2016102238A patent/AU2016102238A4/en not_active Ceased
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