CN103588705A - Synthetic method of 3-chlorine-2-hydrazinopyridine - Google Patents
Synthetic method of 3-chlorine-2-hydrazinopyridine Download PDFInfo
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- CN103588705A CN103588705A CN201310471317.9A CN201310471317A CN103588705A CN 103588705 A CN103588705 A CN 103588705A CN 201310471317 A CN201310471317 A CN 201310471317A CN 103588705 A CN103588705 A CN 103588705A
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- CN
- China
- Prior art keywords
- hydrazinopyridine
- hydrazine hydrate
- chlorine
- chloro
- synthetic method
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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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
Abstract
The invention discloses a synthetic method of 3-chlorine-2-hydrazinopyridine. The synthetic method is characterized by comprising the following steps: uniformly mixing 2-fluorine-3-chloropyridine and hydrazine hydrate, adding an alcohol solvent, reacting for 3-5 hours at a room temperature, drying the solvent, and carrying out rotary evaporation, thus obtaining the 3-chlorine-2-hydrazinopyridine. The synthetic method of the 3-chlorine-2-hydrazinopyridine has the advantages that the operation process is simple, the high-yield high-quality product can be obtained without heating flux, the product yield can reach 99.53%, and the product purity can reach 99.95%.
Description
Technical field
The synthetic method that the present invention relates to chloro-2 hydrazino pyridines of a kind of 3-, belongs to field of fine chemical.
Background technology
3-chloride-2-hydrazinopyridine is the important intermediate of synthesizing new ryanodine receptor sterilant chlorine worm benzene methanamine and cyanogen insect amide.This insecticides Main Function, in insect calcium channel, makes the property anesthesia of flaccid muscles of insect.About the preparation of 3-chloride-2-hydrazinopyridine, main a large amount of hydrazine hydrates and 2, the 3-dichloropyridine of adopting reacts at present, in foreign patent WO2008/134969 A1, use dioxane to make solvent, back flow reaction obtains 2 in 20 hours, 3-dichloropyridine, product yield is 71%; Chinese patent CN101550130A is directly by 2,3-dichloropyridine and hydrazine hydrate back flow reaction 4 hours, yield 68.5%; In aforesaid method, the yield of chloro-2 hydrazino pyridines of 3-is all relatively low, waste of material, and cost is high-leveled and difficult effectively to carry out in suitability for industrialized production.And in Chinese patent CN102249991 A, with 2,3-dichloropyridine and hydrazine hydrate are raw material, add polar solvent (methyl alcohol, ethanol, dimethyl formamide, N,N-DIMETHYLACETAMIDE, tetrahydrofuran (THF)), after back flow reaction 4-8 hour, be down to room temperature suction filtration and obtain chloro-2 hydrazino pyridines of 3-, the yield of this kind of method product can reach 95%-99%, but the raw material of this kind of method is 2,3-dichloropyridine, the leaving away property of chlorine is not high, needs the heating reflux reaction long period just can remove, unsatisfactory aspect economy.
Summary of the invention
The object of this invention is to provide in a kind of reaction process does not need reflux just can obtain the chloro-2 hydrazino pyridine synthetic methods of 3-of high purity, high yield.
The present invention is achieved through the following technical solutions: after the fluoro-3-chloropyridine of 2-and hydrazine hydrate are mixed, add alcohol solvent, after room temperature reaction 3-5 hour, that solvent draws is dry, revolve steaming obtains 3-chloride-2-hydrazinopyridine.
Preferably, the mol ratio of the fluoro-3-chloropyridine of above-mentioned 2-and hydrazine hydrate is 1:1-4.
Preferably, the massfraction of above-mentioned hydrazine hydrate is 80%.
Preferably, the massfraction of above-mentioned ethanol is 95%.
Preferably, the volume ratio of above-mentioned hydrazine hydrate and ethanol is 1:1.
The preparation method of 3-chloride-2-hydrazinopyridine of the present invention, operating process is simple, without reflux, can obtain the high-quality product of high yield, and product yield can reach 99.53%, and product purity can reach 99.95%.
Embodiment
Embodiment mono-: after the fluoro-3-chloropyridine of 1mol 2-and 1mol hydrazine hydrate are mixed, add and the isopyknic alcohol solvent of hydrazine hydrate, after room temperature reaction 3-5 hour, that solvent draws is dry, revolve steaming obtains 3-chloride-2-hydrazinopyridine, product yield is 97.93%, and product purity is 99.15%.
Embodiment bis-: after the fluoro-3-chloropyridine of 1mol 2-and 2mol hydrazine hydrate are mixed, add and the isopyknic alcohol solvent of hydrazine hydrate, after room temperature reaction 3-5 hour, that solvent draws is dry, revolve steaming obtains 3-chloride-2-hydrazinopyridine, product yield is 98.93%, and product purity is 99.37%.
Embodiment tri-: after the fluoro-3-chloropyridine of 1mol 2-and 3mol hydrazine hydrate are mixed, add and the isopyknic alcohol solvent of hydrazine hydrate, after room temperature reaction 3-5 hour, that solvent draws is dry, revolve steaming obtains 3-chloride-2-hydrazinopyridine, product yield is 99.53%, and product purity is 99.95%.
Embodiment tetra-: after the fluoro-3-chloropyridine of 1mol 2-and 4mol hydrazine hydrate are mixed, add and the isopyknic alcohol solvent of hydrazine hydrate, after room temperature reaction 3-5 hour, that solvent draws is dry, revolve steaming obtains 3-chloride-2-hydrazinopyridine, product yield is 99.32%, and product purity is 99.88%.
Claims (5)
1. the chloro-2 hydrazino pyridine synthetic methods of 3-, is characterized in that, after the fluoro-3-chloropyridine of 2-and hydrazine hydrate are mixed, add alcohol solvent, and after room temperature reaction 3-5 hour, that solvent draws is dry, revolve steaming obtains 3-chloride-2-hydrazinopyridine.
2. the chloro-2 hydrazino pyridine synthetic methods of 3-according to claim 1, is characterized in that, the mol ratio of the fluoro-3-chloropyridine of described 2-and hydrazine hydrate is 1:1-4.
3. the chloro-2 hydrazino pyridine synthetic methods of 3-according to claim 1, is characterized in that, the massfraction of described hydrazine hydrate is 80%.
4. the chloro-2 hydrazino pyridine synthetic methods of 3-according to claim 1, is characterized in that, the massfraction of described ethanol is 95%.
5. the chloro-2 hydrazino pyridine synthetic methods of 3-according to claim 1, is characterized in that, described hydrazine hydrate and the volume ratio of ethanol are 1:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310471317.9A CN103588705A (en) | 2013-10-11 | 2013-10-11 | Synthetic method of 3-chlorine-2-hydrazinopyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310471317.9A CN103588705A (en) | 2013-10-11 | 2013-10-11 | Synthetic method of 3-chlorine-2-hydrazinopyridine |
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| Publication Number | Publication Date |
|---|---|
| CN103588705A true CN103588705A (en) | 2014-02-19 |
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| CN201310471317.9A Pending CN103588705A (en) | 2013-10-11 | 2013-10-11 | Synthetic method of 3-chlorine-2-hydrazinopyridine |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748992A (en) * | 2017-01-04 | 2017-05-31 | 安徽国星生物化学有限公司 | A kind of synthetic method of the trichloromethyl pyridine of 3 chlorine, 2 diazanyl 5 |
| CN114057632A (en) * | 2022-01-19 | 2022-02-18 | 苏州开元民生科技股份有限公司 | Environment-friendly synthesis method of 3-chloro-2-hydrazinopyridine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249991A (en) * | 2011-06-01 | 2011-11-23 | 河南中医学院 | Method for high-yield synthesis of 3-chloride-2-hydrazinopyridine |
| CN102584694A (en) * | 2012-01-06 | 2012-07-18 | 华东理工大学 | Preparation methods for important intermediates of anthranilic diamide compound |
-
2013
- 2013-10-11 CN CN201310471317.9A patent/CN103588705A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249991A (en) * | 2011-06-01 | 2011-11-23 | 河南中医学院 | Method for high-yield synthesis of 3-chloride-2-hydrazinopyridine |
| CN102584694A (en) * | 2012-01-06 | 2012-07-18 | 华东理工大学 | Preparation methods for important intermediates of anthranilic diamide compound |
Non-Patent Citations (3)
| Title |
|---|
| HAIXIA WANG等: "Generation of 3,8-substituted 1,2,4-trizolopyridines as potent inhibitors of human 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1)", 《BIOORGANIC &MEDICINAL CHEMISTRY LETTERS》, vol. 21, no. 4, 15 July 2011 (2011-07-15), pages 4146 - 4149 * |
| 张应鹏，等: "新型3-溴-1-(3-氯-2-吡啶)-1H-吡唑甲酰胺类化合物的合成", 《兰州理工大学》, vol. 37, no. 1, 28 February 2011 (2011-02-28), pages 63 - 66 * |
| 高宁，等: "吡唑酸类化合物的合成研究", 《化学研究》, no. 3, 31 May 2011 (2011-05-31) * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748992A (en) * | 2017-01-04 | 2017-05-31 | 安徽国星生物化学有限公司 | A kind of synthetic method of the trichloromethyl pyridine of 3 chlorine, 2 diazanyl 5 |
| CN114057632A (en) * | 2022-01-19 | 2022-02-18 | 苏州开元民生科技股份有限公司 | Environment-friendly synthesis method of 3-chloro-2-hydrazinopyridine |
| CN114057632B (en) * | 2022-01-19 | 2022-11-08 | 苏州开元民生科技股份有限公司 | Environment-friendly synthesis method of 3-chloro-2-hydrazinopyridine |
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Application publication date: 20140219 |