CN111170937A - Preparation method of 3-aminopyridine - Google Patents
Preparation method of 3-aminopyridine Download PDFInfo
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- CN111170937A CN111170937A CN202010017180.XA CN202010017180A CN111170937A CN 111170937 A CN111170937 A CN 111170937A CN 202010017180 A CN202010017180 A CN 202010017180A CN 111170937 A CN111170937 A CN 111170937A
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- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 48
- 239000005708 Sodium hypochlorite Substances 0.000 claims abstract description 33
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 33
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 24
- 229960003966 nicotinamide Drugs 0.000 claims abstract description 16
- 235000005152 nicotinamide Nutrition 0.000 claims abstract description 16
- 239000011570 nicotinamide Substances 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 238000006731 degradation reaction Methods 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 16
- 239000012043 crude product Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 238000004321 preservation Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000007670 refining Methods 0.000 claims description 6
- 238000002390 rotary evaporation Methods 0.000 claims description 6
- 238000005070 sampling Methods 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000003828 vacuum filtration Methods 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 150000003927 aminopyridines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- -1 aminopyridine compounds Chemical class 0.000 description 2
- 239000013064 chemical raw material Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- RUPDGJAVWKTTJW-UHFFFAOYSA-N 2,3-dinitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1[N+]([O-])=O RUPDGJAVWKTTJW-UHFFFAOYSA-N 0.000 description 1
- HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07D213/73—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention relates to a preparation method of 3-aminopyridine. The method takes nicotinamide as an initial raw material, performs Hofmann degradation reaction in sodium hypochlorite and sodium hydroxide solution, and obtains the final 3-aminopyridine product through reaction cooling treatment, alkali adjustment, heating reaction treatment, vacuum filtration drying and secondary recrystallization drying. The whole reaction condition is mild and easy to control, the operation is simple, the purity of the 3-aminopyridine reaches more than 99 percent, the post-treatment method is simple and convenient, the operation is easy, the total yield can reach more than 90 percent, and the method is a post-treatment technology suitable for industrial production and application.
Description
Technical Field
The invention relates to the field of chemical raw material synthesis, in particular to a preparation method of 3-aminopyridine.
Background
Aminopyridine is an important derivative of pyridine and has wide application in the field of chemistry and chemical engineering. With the continuous development of scientific technology, the application range of aminopyridine compounds is on the rising trend year by year. Wherein, the 3-aminopyridine is one of the main aminopyridine compounds and is mainly used for synthesizing pesticides and medical intermediates. The current method for preparing 3-aminopyridine mainly comprises the following process routes: firstly, halogenated pyridine compounds are catalyzed and synthesized; secondly, the catalyst is synthesized by catalytic reduction of nitropyridine; thirdly, cyanopyridine is hydrolyzed and then synthesized by Hofmann degradation; fourthly, the pyridine is synthesized by acid amine of picoline and then Hofmann degradation; fifthly, formamide is directly synthesized by Hofmann degradation.
Compared with the preparation method, the method has the advantages that the initial raw material halogenated pyridine used in the first method is difficult to synthesize and expensive, the cost is increased due to the use of a metal catalyst in the reaction process, and the method is difficult to treat waste water and is not advisable. The method has harsh synthesis conditions of the dinitropyridine, lower yield, higher cost and non-mild conditions during the synthesis of the aminopyridine, and is not advisable. In the method, cyanopyridine serving as a raw material is low in price, reaction conditions are mild, the method is common, and the hydrolysis of cyanopyridine is followed by further Hofmann degradation reaction, so that the total yield of the reaction is not too high. In the fourth method, the picoline is firstly synthesized into acid amine and then subjected to Hofmann degradation to obtain the aminopyridine, the synthesis steps are more, and the final yield is lower, so that the method is not advisable. In the method five, formamide is directly used as a raw material, and aminopyridine is synthesized in a sodium hypobromite solution through Hofmann degradation.
As 3-aminopyridine is an important chemical raw material and has large market demand, the research and development of the environment-friendly, efficient and economic 3-aminopyridine preparation method suitable for industrial production has great significance.
Disclosure of Invention
The invention aims to provide a preparation method of 3-aminopyridine, which is characterized by simple process, convenient operation and high product yield and is a more typical cleaning process.
The technical scheme adopted by the invention for solving the technical problems is as follows: a preparation method of 3-aminopyridine is characterized in that nicotinamide is used as a raw material, and Hofmann degradation reaction is carried out in a sodium hypochlorite solution and a 10% sodium hydroxide solution, and the preparation method specifically comprises the following steps:
s1: firstly, carrying out cooling and stirring treatment on a sodium hypochlorite solution;
s2: when the temperature of the sodium hypochlorite solution is lower than 20 ℃, adding solid nicotinamide into the sodium hypochlorite solution, simultaneously keeping the temperature of the reaction solution at 0-20 ℃ so as to carry out low-temperature reaction, and continuously stirring until the reaction solution is clear;
s3: testing the pH value of the reaction solution, detecting whether the raw materials are completely converted by HPLC, adding a 10% sodium hydroxide solution, adjusting the reaction solution to be strongly alkaline, transferring the reaction solution to a water bath, slowly heating, and carrying out heat preservation reaction for a certain time;
s4: sampling and detecting by HPLC (high performance liquid chromatography) at regular time during the reaction period of the step S3 until the content of the product is more than or equal to 98 percent and the reaction is finished;
s5: performing rotary evaporation, concentration and suction filtration on the reaction solution after the reaction in the step S4, and extracting by using an organic solvent to obtain a crude product of the 3-aminopyridine;
s6: and recrystallizing and refining the crude product of the 3-aminopyridine to obtain a light yellow or white solid, and drying in vacuum to obtain the product of the 3-aminopyridine.
Preferably, the mass ratio of the nicotinamide to the sodium hypochlorite solution to the 10% sodium hydroxide solution is 1: (4.5-20): (0.6-2.5), wherein the effective chlorine content of the sodium hypochlorite solution is 3% -12%.
Preferably, the mass ratio of the nicotinamide to the sodium hypochlorite solution to the 10% sodium hydroxide solution is 1:7.7:0.96, and the available chlorine content of the sodium hypochlorite solution is 7.5%.
As optimization, the low-temperature reaction temperature in the step S2 is 0-20 ℃, and the low-temperature reaction time is 10-120 min.
In the step S3, the heat preservation reaction temperature is 50-80 ℃, and the heat preservation reaction time is 0.5-3 h.
As optimization, the low-temperature reaction temperature in the step S2 is 5-10 ℃, and the low-temperature reaction time is 30-60 min.
In the step S3, the heat preservation reaction temperature is 70-75 ℃, and the heat preservation reaction time is 1-1.5 h.
The invention has the beneficial effects that: the invention takes nicotinamide as the initial raw material, and the nicotinamide is subjected to Hofmann degradation reaction in sodium hypochlorite solution and sodium hydroxide solution, the reaction conditions are mild and easy to control, the operation is simple, the purity of the product 3-aminopyridine reaches more than 99 percent, the post-treatment method is simple and convenient, the operation is easy, the total yield can reach more than 90 percent, and the invention is a post-treatment technology suitable for industrial production and application.
Detailed Description
The method for preparing 3-aminopyridine by Hofmann degradation has a reaction formula:
the experimental steps are as follows:
putting a quantitative sodium hypochlorite solution into a four-neck flask, putting the four-neck flask into a 0 ℃ cold trap to cool, and simultaneously starting stirring. When the sodium hypochlorite solution in the four-mouth flask is cooled to a certain temperature, adding the solid raw material nicotinamide, controlling the temperature in the flask, and continuing stirring and reacting for a certain time after the feed liquid is stirred to be clear. Testing the pH value, detecting whether the raw materials are completely converted into an intermediate by using HPLC (high performance liquid chromatography), then adding a quantitative sodium hydroxide solution, adjusting the feed liquid to be strongly alkaline, transferring the feed liquid to a water bath pan, slowly heating, carrying out heat preservation reaction for a certain time, sampling the HPLC for detection at regular time during the reaction period until the content of the product is more than or equal to 98%, and finishing the reaction.
And (3) carrying out rotary evaporation, concentration and suction filtration on the reaction liquid, and extracting by using an organic solvent to obtain a crude product of the 3-aminopyridine. And recrystallizing and refining the crude product of the 3-aminopyridine to obtain a light yellow or white solid, and drying in vacuum to obtain the product of the 3-aminopyridine.
Wherein the mass ratio of the nicotinamide to the sodium hypochlorite solution to the 10% sodium hydroxide solution is 1: (4.5-20): (0.6-2.5), wherein the effective chlorine content of the sodium hypochlorite solution is 3% -12%.
Preferably, the mass ratio of the nicotinamide to the sodium hypochlorite solution to the 10% sodium hydroxide solution is 1:7.7:0.96, and the available chlorine content of the sodium hypochlorite solution is 7.5%.
In order to further improve the purity and the total yield of the 3-aminopyridine, 14 groups of experiments are carried out, and data analysis is carried out.
Example 7:
a preparation method of 3-aminopyridine comprises the following steps:
s1: firstly, 1200g of sodium hypochlorite solution with the effective chlorine content of 3% is subjected to cooling and stirring treatment;
s2: when the temperature of the sodium hypochlorite solution is lower than 20 ℃, adding 60g of solid nicotinamide into the sodium hypochlorite solution, simultaneously keeping the temperature of the reaction solution at 0-20 ℃ so as to carry out low-temperature reaction for 10-120 min, and continuously stirring until the reaction solution is clear;
s3: testing the pH value of the reaction solution, detecting whether the raw materials are completely converted by HPLC, adding 150g of 10% sodium hydroxide solution, adjusting the reaction solution to be strong alkaline, transferring the reaction solution to a water bath, slowly heating to control the temperature to be 50-80 ℃, and keeping the temperature for 0.5-3 h;
s4: sampling and detecting by HPLC (high performance liquid chromatography) at regular time during the reaction period of the step S3 until the content of the product is more than or equal to 98 percent and the reaction is finished;
s5: performing rotary evaporation, concentration and suction filtration on the reaction solution after the reaction in the step S4, and extracting by using an organic solvent to obtain a crude product of the 3-aminopyridine;
s6: and recrystallizing and refining the crude product of the 3-aminopyridine to obtain a light yellow or white solid, and drying in vacuum to obtain the product of the 3-aminopyridine.
Example 12:
a preparation method of 3-aminopyridine comprises the following steps:
s1: firstly, 580g of sodium hypochlorite solution with the effective chlorine content of 7.5 percent is subjected to cooling and stirring treatment;
s2: when the temperature of the sodium hypochlorite solution is lower than 20 ℃, adding 75g of solid nicotinamide into the sodium hypochlorite solution, simultaneously keeping the temperature of the reaction solution at 5-10 ℃ so as to carry out low-temperature reaction for 30-60 min, and continuously stirring until the reaction solution is clear;
s3: testing the pH value of the reaction solution, detecting whether the raw materials are completely converted by HPLC, adding 72g of 10% sodium hydroxide solution, adjusting the reaction solution to be strong alkaline, transferring the reaction solution to a water bath, slowly heating to control the temperature to be 70-75 ℃, and keeping the temperature for 1-1.5 h;
s4: sampling and detecting by HPLC (high performance liquid chromatography) at regular time during the reaction period of the step S3 until the content of the product is more than or equal to 98 percent and the reaction is finished;
s5: performing rotary evaporation, concentration and suction filtration on the reaction solution after the reaction in the step S4, and extracting by using an organic solvent to obtain a crude product of the 3-aminopyridine;
s6: and recrystallizing and refining the crude product of the 3-aminopyridine to obtain a light yellow or white solid, and drying in vacuum to obtain the product of the 3-aminopyridine.
Example 14:
a preparation method of 3-aminopyridine comprises the following steps:
s1: firstly, 365g of sodium hypochlorite solution with 12 percent of available chlorine content is cooled and stirred;
s2: when the temperature of the sodium hypochlorite solution is lower than 20 ℃, adding 75g of solid nicotinamide into the sodium hypochlorite solution, keeping the temperature of the reaction solution at 5 ℃ so as to carry out low-temperature reaction for 40min, and continuously stirring until the reaction solution is clear;
s3: testing the pH value of the reaction solution, detecting whether the raw materials are completely converted by HPLC, adding 45g of 10% sodium hydroxide solution, adjusting the reaction solution to be strongly alkaline, transferring the reaction solution to a water bath, slowly heating to control the temperature to be 70 ℃, and keeping the temperature for 1 h;
s4: sampling and detecting by HPLC (high performance liquid chromatography) at regular time during the reaction period of the step S3 until the content of the product is more than or equal to 98 percent and the reaction is finished;
s5: performing rotary evaporation, concentration and suction filtration on the reaction solution after the reaction in the step S4, and extracting by using an organic solvent to obtain a crude product of the 3-aminopyridine;
s6: and recrystallizing and refining the crude product of the 3-aminopyridine to obtain a light yellow or white solid, and drying in vacuum to obtain the product of the 3-aminopyridine.
Example 7, example 12, example 14 and other example data:
the analysis and calculation of the experiment of 1 to 14 examples show that the total purity of the 3-aminopyridine product can reach 99.5 percent when the example 12 is adopted, and the total yield can reach 92.3 percent.
The above embodiments are only specific examples of the present invention, and the protection scope of the present invention includes but is not limited to the product forms and styles of the above embodiments, and any suitable changes or modifications made by those skilled in the art according to the claims of the present invention shall fall within the protection scope of the present invention.
Claims (7)
1. A preparation method of 3-aminopyridine is characterized in that nicotinamide is used as a raw material, and Hofmann degradation reaction is carried out in a sodium hypochlorite solution and a 10% sodium hydroxide solution, and the preparation method specifically comprises the following steps:
s1: firstly, carrying out cooling and stirring treatment on a sodium hypochlorite solution;
s2: when the temperature of the sodium hypochlorite solution is lower than 20 ℃, adding solid nicotinamide into the sodium hypochlorite solution, simultaneously keeping the temperature of the reaction solution at 0-20 ℃ so as to carry out low-temperature reaction, and continuously stirring until the reaction solution is clear;
s3: testing the pH value of the reaction solution, detecting whether the raw materials are completely converted by HPLC, adding a 10% sodium hydroxide solution, adjusting the reaction solution to be strongly alkaline, transferring the reaction solution to a water bath, slowly heating, and carrying out heat preservation reaction for a certain time;
s4: sampling and detecting by HPLC (high performance liquid chromatography) at regular time during the reaction period of the step S3 until the content of the product is more than or equal to 98 percent and the reaction is finished;
s5: performing rotary evaporation, concentration and suction filtration on the reaction solution after the reaction in the step S4, and extracting by using an organic solvent to obtain a crude product of the 3-aminopyridine;
s6: and recrystallizing and refining the crude product of the 3-aminopyridine to obtain a light yellow or white solid, and drying in vacuum to obtain the product of the 3-aminopyridine.
2. A process for the preparation of 3-aminopyridine according to claim 1, characterized in that: the mass ratio of the nicotinamide to the sodium hypochlorite solution to the 10% sodium hydroxide solution is 1: (4.5-20): (0.6-2.5), wherein the effective chlorine content of the sodium hypochlorite solution is 3% -12%.
3. A process for the preparation of 3-aminopyridine according to claim 1, characterized in that: the mass ratio of the nicotinamide to the sodium hypochlorite solution to the 10% sodium hydroxide solution is 1:7.7:0.96, and the effective chlorine content of the sodium hypochlorite solution is 7.5%.
4. A process for the preparation of 3-aminopyridine according to claim 1, characterized in that: the low-temperature reaction temperature in the step S2 is 0-20 ℃, and the low-temperature reaction time is 10-120 min.
5. A process for the preparation of 3-aminopyridine according to claim 1, characterized in that: in the step S3, the heat preservation reaction temperature is 50-80 ℃, and the heat preservation reaction time is 0.5-3 h.
6. The process according to claim 4, wherein the reaction is carried out in the presence of a catalyst selected from the group consisting of: the low-temperature reaction temperature in the step S2 is 5-10 ℃, and the low-temperature reaction time is 30-60 min.
7. The process according to claim 5, wherein the reaction is carried out in the presence of a catalyst selected from the group consisting of: in the step S3, the heat preservation reaction temperature is 70-75 ℃, and the heat preservation reaction time is 1-1.5 h.
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| CN114436953A (en) * | 2021-10-29 | 2022-05-06 | 陕西菲尔特化工有限公司 | Synthesis process of 3-aminopyridine |
| CN114957030A (en) * | 2021-02-24 | 2022-08-30 | 中国科学院化学研究所 | Chiral cyclic compound and preparation method and application thereof |
| CN116354877A (en) * | 2023-02-10 | 2023-06-30 | 山东泰鲁时代医药科技有限公司 | A kind of synthetic method of 3-aminopyridine |
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| CN114957030A (en) * | 2021-02-24 | 2022-08-30 | 中国科学院化学研究所 | Chiral cyclic compound and preparation method and application thereof |
| CN114957030B (en) * | 2021-02-24 | 2023-09-22 | 中国科学院化学研究所 | Chiral cyclic compound and preparation method and application thereof |
| CN113149896A (en) * | 2021-03-09 | 2021-07-23 | 利尔化学股份有限公司 | Preparation method of 3-aminopyridine |
| CN114436953A (en) * | 2021-10-29 | 2022-05-06 | 陕西菲尔特化工有限公司 | Synthesis process of 3-aminopyridine |
| CN116354877A (en) * | 2023-02-10 | 2023-06-30 | 山东泰鲁时代医药科技有限公司 | A kind of synthetic method of 3-aminopyridine |
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