CN105037254A - Preparation method of 2-pyridyl acrylic acid - Google Patents
Preparation method of 2-pyridyl acrylic acid Download PDFInfo
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- CN105037254A CN105037254A CN201510561706.XA CN201510561706A CN105037254A CN 105037254 A CN105037254 A CN 105037254A CN 201510561706 A CN201510561706 A CN 201510561706A CN 105037254 A CN105037254 A CN 105037254A
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- reaction
- acrylic acid
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- pyridylaldehyde
- pyridyloxy acrylic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
Abstract
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 2-pyridyl acrylic acid. The method includes the following steps of adding malonic acid to be completely dissolved with 2-pyridylaldehyde as the raw material and pyridine as the solvent, then adding a catalyst, raising the temperature to 60-70 DEG C, having a reaction for 2.5 h to 3 h, having a thin-layer chromatography tracking reaction, cooling reaction liquid till the temperature ranges from 0 DEG C to 5 DEG C after the reaction is completed, pouring the reaction liquid into an ice water mixture of concentrated hydrochloric acid, precipitating solid, and conducting pumping filtration to obtain the required product 2-pyridyl acrylic acid. The method has the advantages of being moderate in reaction condition, easy to operate, simple in postprocessing, beneficial to enlarged production, quite suitable for industrial production, good in catalysis effect, high in yield, low in raw material price and low in production cost.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to a kind of preparation method of 2-pyridyloxy acrylic acid.
Background technology
Pyridine and its derivatives is distributed in nature widely.Many plant constituents are as all contained pyridine ring compound in the structure of alkaloid etc., they are the bases producing many important compound, are indispensable raw materials during medicine, agricultural chemicals, dyestuff, tensio-active agent, rubber ingredients, fodder additives, foodstuff additive, tackiness agent etc. are produced.2-pyridyloxy acrylic acid is a kind of important intermediate, and its derivative has radiosensitizing effect.
At present, there is the shortcomings such as yield is low, cost is high, complex process in the synthetic method of the 2-pyridyloxy acrylic acid reported.
Summary of the invention
The object of the invention is to overcome that yield in prior art is low, high in cost of production technical deficiency, provide that a kind of yield is high, the preparation method of the simple 2-pyridyloxy acrylic acid of technique.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows:
A preparation method for 2-pyridyloxy acrylic acid, comprises the following steps: with 2-pyridylaldehyde for raw material, pyridine solvent, add propanedioic acid, add catalyzer after dissolving completely, be warming up to 60-70 DEG C, reaction 2.5-3h, thin-layer chromatography follows the tracks of reaction, question response is complete, reaction solution is cooled to 0-5 DEG C and pours in the mixture of ice and water of concentrated hydrochloric acid again, separates out solid, suction filtration, obtains desired product 2-pyridyloxy acrylic acid.
Further, the mol ratio of described 2-pyridylaldehyde and propanedioic acid is 1:2-2.5.
Further, described catalyzer is piperidines.
Further, the consumption of described piperidines is the 12-15% of described 2-pyridylaldehyde consumption, and described per-cent is mass percent.
Further, a kind of preparation method of 2-pyridyloxy acrylic acid comprises the following steps: with 2-pyridylaldehyde for raw material, pyridine solvent, add propanedioic acid, add catalyzer after dissolving completely, be warming up to 65 DEG C, reaction 3h, thin-layer chromatography follows the tracks of reaction, question response is complete, reaction solution is cooled to 0-5 DEG C and pours in the mixture of ice and water of concentrated hydrochloric acid again, separates out solid, suction filtration, obtains desired product 2-pyridyloxy acrylic acid.
Reaction equation of the present invention is as follows:
Employing the invention has the beneficial effects as follows: reaction conditions is gentle, easy handling, and aftertreatment is simple, easily amplifies production, is very applicable to suitability for industrialized production; Excellent catalytic effect, yield is high; Cost of material is cheap, and production cost is low.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described.These embodiments are illustrative completely, and they are only used for being specifically described the present invention, should not be construed as limitation of the present invention.
Embodiment 1
By 2-pyridine phenyl aldehyde (10.7g, 0.1mol), propanedioic acid (20.4g, 0.2mol) join in 100ml round-bottomed flask, add 30ml pyridine solvent, magnetic agitation, after it all dissolves, 1.3g piperidines is injected in system, oil bath is warming up to 60 DEG C, reaction 2.5h, and thin-layer chromatography follows the tracks of reaction, after question response is complete, reaction solution is cooled to 0-5 DEG C, pours in the mixture of ice and water filling concentrated hydrochloric acid (12mol/l, 50ml), a large amount of white solid is had to separate out, suction filtration, obtains required 2-pyridyloxy acrylic acid, and molar yield is 72%.
Embodiment 2
By 2-pyridine phenyl aldehyde (10.7g, 0.1mol), propanedioic acid (20.4g, 0.2mol) join in 100ml round-bottomed flask, add 30ml pyridine solvent, magnetic agitation, after it all dissolves, 1.3g piperidines is injected in system, oil bath is warming up to 70 DEG C, reaction 2.5h, and thin-layer chromatography follows the tracks of reaction, after question response is complete, reaction solution is cooled to 0-5 DEG C, pours in the mixture of ice and water filling concentrated hydrochloric acid (12mol/l, 50ml), a large amount of white solid is had to separate out, suction filtration, obtains required 2-pyridyloxy acrylic acid, and molar yield is 72%.
Embodiment 3
By 2-pyridine phenyl aldehyde (10.7g, 0.1mol), propanedioic acid (23.5g, 0.23mol) join in 100ml round-bottomed flask, add 30ml pyridine solvent, magnetic agitation, after it all dissolves, 1.4g piperidines is injected in system, oil bath is warming up to 65 DEG C, reaction 2.5h, and thin-layer chromatography follows the tracks of reaction, after question response is complete, reaction solution is cooled to 0-5 DEG C, pours in the mixture of ice and water filling concentrated hydrochloric acid (12mol/l, 50ml), a large amount of white solid is had to separate out, suction filtration, obtains required 2-pyridyloxy acrylic acid, and molar yield is 76%.
Embodiment 4
By 2-pyridine phenyl aldehyde (10.7g, 0.1mol), propanedioic acid (25.5g, 0.25mol) join in 100ml round-bottomed flask, add 30ml pyridine solvent, magnetic agitation, after it all dissolves, 1.6g piperidines is injected in system, oil bath is warming up to 65 DEG C, reaction 3h, and thin-layer chromatography follows the tracks of reaction, after question response is complete, reaction solution is cooled to 0-5 DEG C, pours in the mixture of ice and water filling concentrated hydrochloric acid (12mol/l, 50ml), a large amount of white solid is had to separate out, suction filtration, obtains required 2-pyridyloxy acrylic acid, and molar yield is 78%.
Claims (5)
1. a preparation method for 2-pyridyloxy acrylic acid, is characterized in that comprising the following steps: with 2-pyridylaldehyde for raw material, pyridine solvent, add propanedioic acid, add catalyzer after dissolving completely, be warming up to 60-70 DEG C, reaction 2.5-3h, thin-layer chromatography follows the tracks of reaction, question response is complete, reaction solution is cooled to 0-5 DEG C and pours in the mixture of ice and water of concentrated hydrochloric acid again, separates out solid, suction filtration, obtains desired product 2-pyridyloxy acrylic acid.
2. the preparation method of a kind of 2-pyridyloxy acrylic acid according to claim 1, is characterized in that the mol ratio of described 2-pyridylaldehyde and propanedioic acid is 1:2-2.5.
3. the preparation method of a kind of 2-pyridyloxy acrylic acid according to claim 1, is characterized in that described catalyzer is piperidines.
4. the preparation method of a kind of 2-pyridyloxy acrylic acid according to claim 3, it is characterized in that the consumption of described piperidines is the 12-15% of described 2-pyridylaldehyde consumption, described per-cent is mass percent.
5. the preparation method of a kind of 2-pyridyloxy acrylic acid according to claim 1, is characterized in that comprising the following steps: with 2-pyridylaldehyde for raw material, pyridine solvent, add propanedioic acid, add catalyzer after dissolving completely, be warming up to 65 DEG C, reaction 3h, thin-layer chromatography follows the tracks of reaction, question response is complete, reaction solution is cooled to 0-5 DEG C and pours in the mixture of ice and water of concentrated hydrochloric acid again, separates out solid, suction filtration, obtains desired product 2-pyridyloxy acrylic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510561706.XA CN105037254A (en) | 2015-09-07 | 2015-09-07 | Preparation method of 2-pyridyl acrylic acid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510561706.XA CN105037254A (en) | 2015-09-07 | 2015-09-07 | Preparation method of 2-pyridyl acrylic acid |
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| CN105037254A true CN105037254A (en) | 2015-11-11 |
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| CN201510561706.XA Pending CN105037254A (en) | 2015-09-07 | 2015-09-07 | Preparation method of 2-pyridyl acrylic acid |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06113870A (en) * | 1992-10-09 | 1994-04-26 | Mitsui Toatsu Chem Inc | Production of beta-substituted alanine derivative |
| WO2002096858A1 (en) * | 2001-05-31 | 2002-12-05 | Bristol-Myers Squibb Company | Cinnamide derivatives as kcnq potassium channel modulators |
-
2015
- 2015-09-07 CN CN201510561706.XA patent/CN105037254A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06113870A (en) * | 1992-10-09 | 1994-04-26 | Mitsui Toatsu Chem Inc | Production of beta-substituted alanine derivative |
| WO2002096858A1 (en) * | 2001-05-31 | 2002-12-05 | Bristol-Myers Squibb Company | Cinnamide derivatives as kcnq potassium channel modulators |
Non-Patent Citations (2)
| Title |
|---|
| BROWN, THOMAS H.等: "Isocytosine H2-receptor histamine antagonists. II. Synthesis and evaluation of biological activity at histamine H1- and H2-receptors of 5-(heterocyclyl)methylisocytosines", 《 JOURNAL OF MEDICINAL CHEMISTRY》 * |
| C. S. MARVEL等: "PYRIDINE ANALOGS OF CHALCONE AND THEIR POLYMERIZATION", 《J. ORG. CHEM.》 * |
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