CN103664757A - Preparation method of 2-hydroxy-3-nitropyridine - Google Patents
Preparation method of 2-hydroxy-3-nitropyridine Download PDFInfo
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- CN103664757A CN103664757A CN201310646492.7A CN201310646492A CN103664757A CN 103664757 A CN103664757 A CN 103664757A CN 201310646492 A CN201310646492 A CN 201310646492A CN 103664757 A CN103664757 A CN 103664757A
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- hydroxy
- nitropyridine
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- pyridine
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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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a preparation method of 2-hydroxy-3-nitropyridine. The method comprises the following steps: dropwise adding nitric acid into 2-hydroxypyridine dissolved in pyridine, placing a reaction bottle containing the 2-hydroxypyridine solution in an ice bath, taking out the reaction bottle after the addition, and reacting for 20-40 min while stirring at room temperature; and concentrating the pyridine in the reaction bottle to half of the original volume, repeating the operations in the step (1) for 3-5 times, then adding alkaline into the obtained mixed solution in to a neutral state, and conducting posttreatment to obtain 2-hydroxy-3-nitropyridine. Through the above way, the 2-hydroxy-3-nitropyridine obtained by the preparation method of 2-hydroxy-3-nitropyridine provided by the invention has high purity and can be directly applied to the subsequent production without other treatment process. The method produces little waste liquid and waste gas in the preparation process, greatly reduces the pollutants discharged into the environment, and is conducive to the green production and suitable for large-scale promotion and application.
Description
Technical field
The present invention relates to Minute Organic Synthesis field, particularly relate to a kind of preparation method of 2-hydroxy-3-nitropyridine.
Background technology
The molecular formula of 2-hydroxy-3-nitropyridine is C
5h
4n
2o
3, molecular weight is 140.09686, and fusing point is 212 ℃, and yellow needle-like crystal is insoluble in benzene, ether, sherwood oil and cold water, is dissolved in hot water and hot alcohol, is soluble in diluted alkaline, and eyes, respiratory system and skin are had to hormesis, and minority report has carcinogenic consequence.2-hydroxy-3-nitropyridine is used widely in fields such as medicine, agricultural chemicals and organic syntheses, can be used in synthetic 2-ethanoyl-3-aminopyridine, the bromo-3-aminopyridine of 2-, 3-amino-2-bromopyridine mono-hydrochloric salts and the bromo-3-nitropyridine of 2-.In the process of the synthetic 2-hydroxy-3-nitropyridine of tradition, can produce a large amount of organic liquid wastes, these discharging of waste liquid pollute the environment in environment, are unfavorable for environment protection.
Summary of the invention
The technical problem that the present invention mainly solves is to provide a kind of preparation method of 2-hydroxy-3-nitropyridine, and the method is simple to operate and safe and reliable.
For solving the problems of the technologies described above, the technical scheme that the present invention adopts is: a kind of preparation method of 2-hydroxy-3-nitropyridine is provided, comprises that step is:
(1) toward the 2 hydroxy pyrimidine being dissolved in pyridine, drip nitric acid, the reaction flask that fills described 2 hydroxy pyrimidine solution is placed in ice bath, drips and finishes rear taking-up reaction flask, stirring reaction 20-40 minute under room temperature;
(2) pyridine in described reaction flask is concentrated to after half volume, the operation of repeating step (1), repeats 3-5 time, then adds alkali to neutral in the mixed solution obtaining, and aftertreatment obtains 2-hydroxy-3-nitropyridine.
In a preferred embodiment of the present invention, described in step (1), the mass percent of nitric acid is 60-75%.
In a preferred embodiment of the present invention, described in step (2), alkali is sodium hydroxide, sodium carbonate or sodium bicarbonate.
In a preferred embodiment of the present invention, described in step (2), add reaction flask described in the process of alkali and be placed in ice bath.
The invention has the beneficial effects as follows: the preparation method of 2-hydroxy-3-nitropyridine of the present invention, the 2-hydroxy-3-nitropyridine purity obtaining is high, do not need to carry out other treating processes, can be applied directly in follow-up production, the waste liquid waste gas that the method preparation process produces is few, the pollutent being discharged in environment greatly reduces, and is conducive to greenization and produces, and can apply on a large scale.
Embodiment
Below the technical scheme in the embodiment of the present invention is clearly and completely described, obviously, described embodiment is only a part of embodiment of the present invention, rather than whole embodiment.Embodiment based in the present invention, those of ordinary skills, not making all other embodiment that obtain under creative work prerequisite, belong to the scope of protection of the invention.
Embodiment mono-:
A kind of preparation method of 2-hydroxy-3-nitropyridine is provided, comprises that step is:
(1) toward the 2 hydroxy pyrimidine being dissolved in pyridine, drip the nitric acid that mass percent is 67%, the reaction flask that fills described 2 hydroxy pyrimidine solution is placed in ice bath, drips and finishes rear taking-up reaction flask, and under room temperature, stirring reaction is 30 minutes;
(2) pyridine in described reaction flask is concentrated to after half volume, the operation of repeating step (1), repeats 3 times, then adds sodium bicarbonate to neutral in the mixed solution obtaining, add reaction flask described in the process of alkali and be placed in ice bath, aftertreatment obtains 2-hydroxy-3-nitropyridine.
Embodiment bis-:
A kind of preparation method of 2-hydroxy-3-nitropyridine is provided, comprises that step is:
(1) toward the 2 hydroxy pyrimidine being dissolved in pyridine, drip the nitric acid that mass percent is 60%, the reaction flask that fills described 2 hydroxy pyrimidine solution is placed in ice bath, drips and finishes rear taking-up reaction flask, and under room temperature, stirring reaction is 30 minutes;
(2) pyridine in described reaction flask is concentrated to after half volume, the operation of repeating step (1), repeats 4 times, then adds sodium carbonate to neutral in the mixed solution obtaining, add reaction flask described in the process of alkali and be placed in ice bath, aftertreatment obtains 2-hydroxy-3-nitropyridine.
Embodiment tri-:
A kind of preparation method of 2-hydroxy-3-nitropyridine is provided, comprises that step is:
(1) toward the 2 hydroxy pyrimidine being dissolved in pyridine, drip the nitric acid that mass percent is 75%, the reaction flask that fills described 2 hydroxy pyrimidine solution is placed in ice bath, drips and finishes rear taking-up reaction flask, and under room temperature, stirring reaction is 25 minutes;
(2) pyridine in described reaction flask is concentrated to after half volume, the operation of repeating step (1), repeats 5 times, then toward hydro-oxidation sodium in the mixed solution obtaining to neutral, add reaction flask described in the process of alkali and be placed in ice bath, aftertreatment obtains 2-hydroxy-3-nitropyridine.
The foregoing is only embodiments of the invention; not thereby limit the scope of the claims of the present invention; every equivalent structure or conversion of equivalent flow process that utilizes description of the present invention to do; or be directly or indirectly used in other relevant technical field, be all in like manner included in scope of patent protection of the present invention.
Claims (4)
1. a preparation method for 2-hydroxy-3-nitropyridine, is characterized in that, comprises that step is:
(1) toward the 2 hydroxy pyrimidine being dissolved in pyridine, drip nitric acid, the reaction flask that fills described 2 hydroxy pyrimidine solution is placed in ice bath, drips and finishes rear taking-up reaction flask, stirring reaction 20-40 minute under room temperature;
(2) pyridine in described reaction flask is concentrated to after half volume, the operation of repeating step (1), repeats 3-5 time, then adds alkali to neutral in the mixed solution obtaining, and aftertreatment obtains 2-hydroxy-3-nitropyridine.
2. the preparation method of 2-hydroxy-3-nitropyridine according to claim 1, is characterized in that, described in step (1), the mass percent of nitric acid is 60-75%.
3. the preparation method of 2-hydroxy-3-nitropyridine according to claim 1, is characterized in that, described in step (2), alkali is sodium hydroxide, sodium carbonate or sodium bicarbonate.
4. the preparation method of 2-hydroxy-3-nitropyridine according to claim 1, is characterized in that, adds reaction flask described in the process of alkali and be placed in ice bath described in step (2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310646492.7A CN103664757A (en) | 2013-12-06 | 2013-12-06 | Preparation method of 2-hydroxy-3-nitropyridine |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310646492.7A CN103664757A (en) | 2013-12-06 | 2013-12-06 | Preparation method of 2-hydroxy-3-nitropyridine |
Publications (1)
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|---|---|
| CN103664757A true CN103664757A (en) | 2014-03-26 |
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|---|---|---|---|
| CN201310646492.7A Pending CN103664757A (en) | 2013-12-06 | 2013-12-06 | Preparation method of 2-hydroxy-3-nitropyridine |
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| CN (1) | CN103664757A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532010A (en) * | 2011-12-25 | 2012-07-04 | 江苏新瀚有限公司 | Preparation method of 2-chloro-3-aminopyridine |
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2013
- 2013-12-06 CN CN201310646492.7A patent/CN103664757A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532010A (en) * | 2011-12-25 | 2012-07-04 | 江苏新瀚有限公司 | Preparation method of 2-chloro-3-aminopyridine |
Non-Patent Citations (3)
| Title |
|---|
| CHUN, KWANGWOO，等: "Synthesis and evaluation of 8-amino-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives as glycogen synthase kinase-3 (GSK-3) inhibitors", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》, vol. 23, no. 13, 4 April 2013 (2013-04-04), pages 3984 - 1, XP028564872, DOI: doi:10.1016/j.bmcl.2013.03.119 * |
| ZAKHS, E. R.，等: "Synthesis and photochromic properties of 2-(3-nitro-2-pyridylmethyl)benzazoles", 《RUSSIAN JOURNAL OF GENERAL CHEMISTRY》, vol. 71, no. 7, 31 July 2001 (2001-07-31), XP001094317, DOI: doi:10.1023/A:1013237222718 * |
| 王晓晨，等: "嘧啶与吡啶衍生物硝化方法的改进", 《化学进展》, vol. 33, no. 3, 31 March 2009 (2009-03-31) * |
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Application publication date: 20140326 |