CN114163352B - Preparation method of 2-methyl-6-nitrobenzaldehyde oxime - Google Patents
Preparation method of 2-methyl-6-nitrobenzaldehyde oxime Download PDFInfo
- Publication number
- CN114163352B CN114163352B CN202210126855.3A CN202210126855A CN114163352B CN 114163352 B CN114163352 B CN 114163352B CN 202210126855 A CN202210126855 A CN 202210126855A CN 114163352 B CN114163352 B CN 114163352B
- Authority
- CN
- China
- Prior art keywords
- methyl
- reaction
- xylene
- nitro
- nitrite
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/06—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by nitrosation of hydrocarbons or substituted hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of 2-methyl-6-nitrobenzaldehyde oxime, which is characterized in that 3-nitro-o-xylene and nitrite react in the presence of alkali and an alcohol-binding agent to prepare the 2-methyl-6-nitrobenzaldehyde oxime. The alcohol-binding agent is added to promote the forward reaction, inhibit the generation of dimer byproducts and improve the yield of 2-methyl-6-nitrobenzaldehyde oxime; the reaction of the invention does not need to be carried out at ultralow temperature, reduces the energy consumption required for maintaining ultralow temperature and the requirement on equipment, has high economic benefit and is suitable for large-scale production.
Description
Technical Field
The invention relates to a preparation method of 2-methyl-6-nitrobenzaldehyde oxime.
Background
Topramezone (Topramezone) is a p-hydroxyphenylpyruvate dioxygenase (HPPD) class of inhibitor herbicides developed by basf corporation, chemical name: 4- [3- (4, 5-dihydroisoxazol-3-yl) -2-methyl-4-methylsulfonyl]-1-methyl-5-hydroxy-1H-pyrazole, of the formula:
. The registered trade names include bract toilet, Clio, Convey and the like, and are mainly used for controlling broad-leaved weeds and gramineous weeds in corn fields. At present, the patent of topramezone technical product is expired, and the development of a new synthesis process with lower cost and equipment requirements and small safety risk is an urgent requirement in the market.
The 3- [ 3-bromo-2-methyl-6- (methylsulfonyl) phenyl ] -4, 5-dihydroisoxazole is the most main intermediate for synthesizing topramezone, and the currently mainstream synthetic methods include the following two methods, namely, reacting 3-nitro-o-xylene serving as a starting material with nitrite as reported in patents CN103788083, US20030216580 and CN101113137 to obtain 2-methyl-6-nitrobenzaldehyde oxime under the action of alkali, and then preparing the intermediate 3- [ 3-bromo-2-methyl-6- (methylsulfonyl) phenyl ] -4, 5-dihydroisoxazole through multiple reactions such as chlorination cyclization, hydrogenation reduction, diazotization (methylthio), bromination, oxidation and the like, wherein the synthetic route is specifically as follows:
the second method is that the raw material 2, 3-dimethylaniline is used as a report in patent US20030216580, diazotized to generate methylthio, brominated and oxidized to obtain 2, 3-dimethyl 4-methylsulfonylbromide, and then the bromobromide and nitrite are subjected to oximation reaction to prepare 2-methyl-3-bromo-6-methylsulfonylbenzaldehyde oxime, and then the 3- [ 3-bromo-2-methyl-6- (methylsulfonyl) phenyl ] -4,5 dihydroisoxazole is obtained through chlorination cyclization reaction, wherein the synthetic route is specifically as follows:
the two methods are not difficult to find that the construction of the benzaldehyde oxime with a functional group is a necessary step for preparing 3- [ 3-bromo-2-methyl-6- (methylsulfonyl) phenyl ] -4, 5-dihydroisoxazole, and the methods for constructing the corresponding benzaldehyde oxime derivative in the first method and the second method are consistent, and both the methods are used for carrying out nucleophilic elimination reaction on ortho-position methyl with a strong electron-withdrawing group and nitrite under the action of alkali, but the biggest defect is that the operation at ultralow temperature (-60 ℃ to-40 ℃) is needed, the industrial production is not facilitated, and the environmental protection requirement is not met; and dimer byproducts are also generated, and are difficult to remove, so that the post-treatment purification difficulty is high, the reaction yield is low and unstable, and the purification of subsequent products is greatly influenced.
Disclosure of Invention
In order to solve the defects in the prior art, the invention aims to provide the preparation method of the 2-methyl-6-nitrobenzaldehyde oxime, which has the advantages of mild reaction conditions, few byproducts, high yield and simple post-treatment.
In order to achieve the purpose, the invention adopts the technical scheme that:
a method for preparing 2-methyl-6-nitrobenzaldehyde oxime comprises the step of reacting 3-nitro-o-xylene with nitrite in the presence of alkali and an alcohol-binding agent to prepare the 2-methyl-6-nitrobenzaldehyde oxime.
Preferably, the alcohol binding agent comprises one or more of calcium chloride, magnesium chloride, zinc chloride, stannous chloride, calcium carbonate, calcium hydroxide and calcium oxide.
Preferably, the feeding molar ratio of the 3-nitro-o-xylene to the alcohol binding agent is 1: (0.1-2).
Further preferably, the feeding molar ratio of the 3-nitro-o-xylene to the alcohol-binding agent is 1: (0.2 to 1).
Still further preferably, the feeding molar ratio of the 3-nitro-o-xylene to the alcohol-binding agent is 1: (0.4-0.6).
Preferably, the reaction temperature is controlled to be-30-0 ℃.
Further preferably, the reaction temperature is controlled to be-10-0 ℃.
Preferably, the reaction time is controlled to be 0.5-18 h.
Preferably, the nitrite comprises one or more of n-butyl nitrite, isoamyl nitrite, tert-butyl nitrite, ethyl nitrite and isobutyl nitrite.
Further preferably, the feeding molar ratio of the 3-nitro-o-xylene to the nitrite is 1: (1-1.5).
Preferably, the base comprises one or more of sodium methoxide, potassium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, sodium cyanide, sodium amide, sodium hydroxide, potassium hydroxide.
Further preferably, the feeding molar ratio of the 3-nitro-o-xylene to the base is 1: (1-2).
Preferably, the preparation method comprises carrying out the reaction in the presence of an organic solvent.
Further preferably, the organic solvent comprises one or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, and N-methylpyrrolidone.
Still further preferably, the feeding mass ratio of the 3-nitro-o-xylene to the organic solvent is 1: (2-20).
Preferably, the preparation method comprises the steps of dissolving the 3-nitro-o-xylene, the nitrite and the alcohol binding agent in an organic solvent, adding the alkali into a reaction system, and controlling the feeding time of the alkali to be 0.2-6 h.
Further preferably, the base is fed in a manner that the base is added to the reaction system in a solid form in portions, or the base is mixed with a solvent and then added dropwise to the reaction system.
Still further preferably, the solvent comprises one or more of N, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran.
Preferably, the preparation method further comprises adding a quenching agent for quenching the reaction into the reaction system, wherein the quenching agent comprises one or more of acetic acid, water, hydrochloric acid, sulfuric acid and phosphoric acid.
Further preferably, the feeding molar ratio of the 3-nitro-o-xylene to the quenching agent is 1: (1-5).
Still more preferably, the quenching agent is charged into the reaction system when the content of the 3-nitro-o-xylene in the reaction system is less than or equal to 0.5%.
Still further preferably, when the quenching agent is acetic acid or hydrochloric acid or sulfuric acid or phosphoric acid, the quenching agent is fed in the form of a quenching agent aqueous solution, and the mass content of the quenching agent in the quenching agent aqueous solution is 40-60%.
Preferably, the preparation method further comprises the steps of mixing the reaction system with ice water after the reaction is finished so as to separate out the 2-methyl-6-nitrobenzaldehyde oxime, and then carrying out suction filtration and drying to obtain the 2-methyl-6-nitrobenzaldehyde oxime.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
the alcohol-binding agent is added to promote the forward reaction, inhibit the generation of dimer byproducts and improve the yield of 2-methyl-6-nitrobenzaldehyde oxime; the reaction of the invention does not need to be carried out at ultralow temperature, reduces the energy consumption and the requirements on equipment required for maintaining ultralow temperature, has high economic benefit and is suitable for large-scale production.
Detailed Description
The present invention will be further described with reference to the following examples. However, the present invention is not limited to the following examples. The implementation conditions adopted in the embodiments can be further adjusted according to different requirements of specific use, and the implementation conditions not mentioned are conventional conditions in the industry. The technical features of the embodiments of the present invention may be combined with each other as long as they do not conflict with each other.
The synthesis of 2-methyl-6-nitrobenzaldehyde oxime by 3-nitro-o-xylene, nitrite and alkali can produce a large amount of alcohols, and the production of the alcohols can inhibit the reaction of intermediate carbonium ions and nitrite, so that the reaction can not be converted into products, thereby leading the carbonium ions to be oxidized into free radicals, and the self-coupling reaction to generate a dimer, wherein the structure of the dimer is shown as III,
thus, the yield and purity of the 2-methyl-6-nitrobenzaldehyde oxime prepared by the method in the prior art are not high.
In addition, in the prior art, the reaction of 3-nitro-o-xylene, nitrite and alkali is harsh, the reaction is generally required to be carried out at an ultralow temperature below-40 ℃, the feeding amount of alkali and nitrite is required to be greatly excessive, the preparation cost is high, the energy consumption is high, the waste of resources is caused to a certain extent, the industrial production is not facilitated, and the environmental protection requirement is not met.
Based on the defects of the prior art, the applicant obtains the scheme of the application through long-term experiments and a large amount of research, and further elaborates on the scheme.
A process for preparing 2-methyl-6-nitrobenzaldehyde oxime includes reaction of 3-nitro-o-xylene (formula I) with nitrite in the presence of alkali and alcohol-binding agent to prepare 2-methyl-6-nitrobenzaldehyde oxime (formula II). The reaction equation is as follows:
the invention creatively adds the alcohol-binding agent, firstly, the reaction of intermediate carbon positive ions and nitrite is promoted by alcohol substances generated in a reaction consumption system of the alcohol-binding agent and alcohol, thus the reaction can be promoted to be rapidly carried out in the forward direction, and the generation of byproduct dimers is avoided, thereby the yield, the purity and the reaction efficiency of the 2-methyl-6-nitrobenzaldehyde oxime can be improved; and secondly, the reaction does not need to be carried out at ultralow temperature, so that the energy consumption required for maintaining the ultralow temperature, the requirement on equipment and the feeding amount of alkali and nitrite are reduced, a better economic effect is achieved, and the method is particularly suitable for industrial production.
According to the invention, the alcohol binding agent comprises one or more of calcium chloride, magnesium chloride, zinc chloride, stannous chloride, calcium carbonate, calcium hydroxide and calcium oxide.
Further, the feeding molar ratio of the 3-nitro-o-xylene to the alcohol-binding agent is 1: (0.1-2). The larger the feeding amount of the alcohol-binding agent is, the less the reaction time is needed for generating the 2-methyl-6-nitrobenzaldehyde oxime, but the excessive feeding amount of the alcohol-binding agent causes reagent waste and increases extra cost; the smaller the amount of the alcohol-binding agent charged, the less the forward progress of the reaction may be promoted, and even if the forward progress of the reaction can be promoted, the reaction time required for producing 2-methyl-6-nitrobenzaldehyde oxime increases, and accordingly the energy consumption required for maintaining the reaction increases, thereby also increasing additional costs. Preferably, the feeding molar ratio of the 3-nitro-o-xylene to the alcohol-binding agent is 1: (0.2 to 1), for example, the ratio of 1: 0.2, 1: 0.3, 1: 0.4, 1: 0.5, 1: 0.6, 1: 0.7, 1: 0.8, 1: 0.9, 1: 1, etc.
According to the invention, the nitrite comprises one or more of n-butyl nitrite, isoamyl nitrite, tert-butyl nitrite, ethyl nitrite and isobutyl nitrite. Further, the feeding molar ratio of the 3-nitro-o-xylene to the nitrite is 1: (1 to 1.5), for example, the ratio of 1: 1. 1: 1.1, 1: 1.2, 1: 1.3, 1: 1.4, 1: 1.5.
according to the invention, the base comprises one or more of sodium methoxide, potassium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, sodium cyanide, sodium amide, sodium hydroxide and potassium hydroxide. Further, the feeding molar ratio of the 3-nitro-o-xylene to the alkali is 1: (1-2), for example, may be 1: 1. 1: 1.1, 1: 1.2, 1: 1.3, 1: 1.4, 1: 1.5, 1: 1.6, 1: 1.7, 1: 1.8, 1: 1.9, 1: 2.
the alkali is preferably fed for 0.2 to 6 hours, more preferably 0.2 to 1 hour, and examples thereof include 0.2 hour, 0.3 hour, 0.4 hour, 0.5 hour, 0.6 hour, 0.7 hour, 0.8 hour, 0.9 hour, and 1 hour.
According to the present invention, the reaction temperature is controlled to-30 to 0 ℃ and may be, for example, -30 ℃, -20 ℃, -15 ℃, -10 ℃, -9 ℃, -8 ℃, -7 ℃, -6 ℃, -5 ℃, -4 ℃, -3 ℃, -2 ℃, -1 ℃, 0 ℃.
According to the invention, the reaction time is controlled to be 0.5-18 h, for example, 0.5h, 1h, 2h, 3h, 4h, 5h, 6h, 7h, 8h, 9h, 10h, 11h, 12h, 13h, 14h, 15h, 16h, 17h, 18h and the like.
According to some specific and preferred embodiments, the process for the preparation of 2-methyl-6-nitrobenzaldehyde oxime comprises the steps of:
(1) dissolving 3-nitro-o-xylene, nitrite and an alcohol binding agent in an organic solvent, adding alkali into the system, and reacting the system at-30-0 ℃ after the addition is finished, wherein the reaction time is controlled to be 0.5-18 h;
(2) when the content of the 3-nitro-o-xylene in the reaction system is less than or equal to 0.5 percent, adding a quenching agent into the reaction system to quench the reaction;
(3) and (3) mixing the reaction system in the step (2) with ice water to separate out the 2-methyl-6-nitrobenzaldehyde oxime, and performing suction filtration and drying to obtain the qualified 2-methyl-6-nitrobenzaldehyde oxime.
According to the present invention, the organic solvent includes one or more of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, and N-methylpyrrolidone. Further, the feeding mass ratio of the 3-nitro-o-xylene to the organic solvent is 1: (2-20), for example, the ratio of 1: 2. 1: 2.5, 1: 3. 1: 3.5, 1: 4. 1: 4.5, 1: 5. 1: 5.5, 1: 6. 1: 6.5, 1: 7, and the like.
According to the invention, the quenching agent comprises one or more of acetic acid, water, hydrochloric acid, sulfuric acid and phosphoric acid. Further, the feeding molar ratio of the 3-nitro-o-xylene to the quenching agent is 1: (1-5), for example, the ratio of 1: 1. 1: 1.5, 1: 2. 1: 3. 1: 4. 1: 5, and the like.
Example 1
Dissolving 3-nitro-o-xylene (1 mol), 108g N-butyl nitrite (1.05 mol) and 55.5g calcium chloride (0.5 mol) in 600 g N, N-dimethylformamide, controlling the temperature at-10 ℃, adding 82g sodium ethoxide (1.2 mol) into the reaction in batches by using a solid feeder under stirring, wherein the adding time is about 30 minutes, controlling the peak area of 3-nitro-o-xylene to be less than 0.1% in GC after the adding is finished and reacting for about 0.5 hour, adding 120 g acetic acid aqueous solution with the mass content of 50% into the system for quenching, pouring the system into 1kg of ice-water mixture under mechanical stirring after the reaction is stable, precipitating a large amount of white solid, carrying out suction filtration after the product is completely precipitated, drying the crude product at 50 ℃ to obtain 175.6 g 2-methyl-6-nitrobenzaldehyde oxime, the product purity was 97%, the quantitative purity was 95.3%, and the quantitative yield was 93% as determined by area normalization.
Example 2
Dissolving 3-nitro-o-xylene (1 mol), 108g N-butyl nitrite (1.05 mol) and 22g calcium chloride (0.2 mol) in 600 g N, N-dimethylformamide, controlling the temperature to be 10 ℃ below zero, adding 88.5 g sodium ethoxide (1.3 mol) into the reaction in batches by a solid feeder under stirring, wherein the adding time is about 40 minutes, controlling the peak area of the 3-nitro-o-xylene to be less than 0.1% in GC after the adding is finished and the reaction is carried out for about 18 hours, adding 120 g acetic acid aqueous solution with the mass content of 50% into the system for quenching, pouring the system into 1kg of ice-water mixture under mechanical stirring after the reaction is stable, precipitating a large amount of white solid, carrying out suction filtration after the product is completely precipitated, drying the crude product at 50 ℃ to obtain 174.1 g of 2-methyl-6-nitrobenzaldehyde oxime, the purity of the product was 95.2%, the quantitative purity was 92%, and the quantitative yield was 89% as determined by area normalization.
Example 3
Dissolving 3 g of nitro-o-xylene (1 mol), 108g of N-butyl nitrite (1.05 mol) and 55.5g of calcium chloride (0.5 mol) in 600 g N, N-dimethylformamide, controlling the temperature to be minus 5 ℃, putting 77 g of potassium methoxide (1.1 mol) into the reaction in batches by using a solid feeder under stirring, wherein the feeding time is about 25 minutes, controlling the peak area of 3-nitro-o-xylene to be less than 0.1% in GC after the completion of the reaction for about 0.5 hour, adding 120 g of acetic acid aqueous solution with the mass content of 50% into the system for quenching, pouring the system into 1kg of ice-water mixture under mechanical stirring after the reaction is stable, precipitating a large amount of white solid, carrying out suction filtration after the product is completely precipitated, drying the crude product at 50 ℃ to obtain 179.6 g of 2-methyl-6-nitrobenzaldehyde oxime, the purity of the product determined by the area normalization method is 98.5%, the quantitative purity is 96% and the quantitative yield is 95.8%.
Comparative example 1
Dissolving 3-nitro-o-xylene (1 mol) 151 g and N-butyl nitrite (1.05 mol) 108g in 600 g N N-dimethylformamide, controlling the temperature at-10 ℃, adding 140 g of potassium methoxide (2 mol) into the reaction in batches by using a solid feeder under stirring, wherein the feeding time is about 9 hours, controlling the peak area of 3-nitro-o-xylene to be less than 3% in GC after the completion of the addition and the reaction for about 6 hours, continuously prolonging the reaction time, keeping the peak area of 3-nitro-o-xylene basically unchanged, preventing the raw materials from being further converted, adding 120 g of acetic acid aqueous solution with the mass content of 50% into the system for quenching, pouring the system into 1kg of ice-water mixture under mechanical stirring after the reaction is stable, precipitating a large amount of white solid, performing suction filtration after the product is completely precipitated, drying the crude product at 50 ℃ to obtain 164 g of 2-methyl-6-nitrobenzaldehyde oxime, the purity of the product was 82%, the quantitative purity was 79% and the quantitative yield was 72% as determined by area normalization.
Comparative example 2
Dissolving 3-nitro-o-xylene (1 mol) 151 g and N-butyl nitrite (1.3 mol) 134 g in 600 g N N-dimethylformamide, controlling the temperature at-40 ℃, adding 175 g of potassium methoxide (2.5 mol) into the reaction in batches by using a solid feeder under stirring, wherein the feeding time is about 9 hours, controlling the peak area of 3-nitro-o-xylene to be less than 1% in GC after the completion of the addition and the reaction is about 6 hours, continuously prolonging the reaction time, keeping the peak area of 3-nitro-o-xylene basically unchanged, adding 120 g of acetic acid aqueous solution with the mass content of 50% into the system for quenching, pouring the system into 1kg of ice-water mixture under mechanical stirring after the reaction is stable, precipitating a large amount of white solid, carrying out suction filtration after the product is completely precipitated, drying the crude product at 50 ℃ to obtain 169.6 g of 2-methyl-6-nitrobenzaldehyde oxime, the purity of the product was 86.5%, the quantitative purity was 83%, and the quantitative yield was 78.2% as determined by area normalization.
The present invention has been described in detail in order to enable those skilled in the art to understand the invention and to practice it, and it is not intended to limit the scope of the invention, and all equivalent changes and modifications made according to the spirit of the present invention should be covered by the present invention.
Claims (12)
1. A preparation method of 2-methyl-6-nitrobenzaldehyde oxime is characterized by comprising the following steps: reacting 3-nitro-o-xylene with nitrite in the presence of alkali and an alcohol-binding agent, wherein the alcohol-binding agent is calcium chloride.
2. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: the feeding molar ratio of the 3-nitro-o-xylene to the alcohol-binding agent is 1: (0.1-2).
3. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 2 wherein: the feeding molar ratio of the 3-nitro-o-xylene to the alcohol-binding agent is 1: (0.2 to 1).
4. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: controlling the temperature of the reaction to be-30-0 ℃,
and/or controlling the reaction time to be 0.5-18 h.
5. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: controlling the reaction temperature to be-10-0 ℃.
6. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: the nitrite is one or more of n-butyl nitrite, isoamyl nitrite, tert-butyl nitrite, ethyl nitrite and isobutyl nitrite;
and/or the feeding molar ratio of the 3-nitro-o-xylene to the nitrite is 1: (1-1.5).
7. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: the alkali is one or more of sodium methoxide, potassium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, sodium cyanide, sodium amide, sodium hydroxide and potassium hydroxide;
and/or the feeding molar ratio of the 3-nitro-o-xylene to the alkali is 1: (1-2).
8. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: the preparation method comprises the step of carrying out reaction in the presence of an organic solvent, wherein the organic solvent is one or more of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone, and the feeding mass ratio of the 3-nitro-o-xylene to the organic solvent is 1: (2-20).
9. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: the preparation method comprises the steps of firstly dissolving the 3-nitro-o-xylene, the nitrite and the alcohol-binding agent in an organic solvent, then adding the alkali into a reaction system, and controlling the feeding time of the alkali to be 0.2-6 h;
the feeding mode of the alkali comprises the step of adding the alkali into the reaction system in batches in a solid form, or adding the alkali into the reaction system dropwise after mixing the alkali with a solvent.
10. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: the preparation method also comprises the step of adding a quenching agent for quenching reaction into the reaction system, wherein the quenching agent is one or more of acetic acid, water, hydrochloric acid, sulfuric acid and phosphoric acid, and the feeding molar ratio of the 3-nitro-o-xylene to the quenching agent is 1: (1-5).
11. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 10 wherein: when the content of the 3-nitro-o-xylene in the reaction system is less than or equal to 0.5 percent, adding the quenching agent into the reaction system;
and/or when the quenching agent is acetic acid, hydrochloric acid, sulfuric acid or phosphoric acid, feeding the quenching agent in the form of a quenching agent aqueous solution, wherein the mass content of the quenching agent in the quenching agent aqueous solution is 40-60%.
12. The method for preparing 2-methyl-6-nitrobenzaldehyde oxime according to claim 1 wherein: and after the reaction is finished, mixing the reaction system with ice water to separate out the 2-methyl-6-nitrobenzaldehyde oxime, and performing suction filtration and drying to obtain the 2-methyl-6-nitrobenzaldehyde oxime.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210126855.3A CN114163352B (en) | 2022-02-11 | 2022-02-11 | Preparation method of 2-methyl-6-nitrobenzaldehyde oxime |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210126855.3A CN114163352B (en) | 2022-02-11 | 2022-02-11 | Preparation method of 2-methyl-6-nitrobenzaldehyde oxime |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114163352A CN114163352A (en) | 2022-03-11 |
| CN114163352B true CN114163352B (en) | 2022-06-10 |
Family
ID=80489686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210126855.3A Active CN114163352B (en) | 2022-02-11 | 2022-02-11 | Preparation method of 2-methyl-6-nitrobenzaldehyde oxime |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114163352B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115784925A (en) * | 2022-10-31 | 2023-03-14 | 江苏七洲绿色科技研究院有限公司 | Continuous preparation method of 2-methyl-6-nitrobenzaldehyde oxime |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030028033A1 (en) * | 1998-11-12 | 2003-02-06 | Deyn Wolfgang Von | Process and novel intermediates for preparing isoxazolin-3-ylacyl benzenes |
| CN103788083A (en) * | 2014-03-10 | 2014-05-14 | 中国药科大学 | Method for preparing herbicide topramezone |
| CN108218851A (en) * | 2018-03-09 | 2018-06-29 | 安徽久易农业股份有限公司 | It is a kind of to improve the method for preparing topramezone |
-
2022
- 2022-02-11 CN CN202210126855.3A patent/CN114163352B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030028033A1 (en) * | 1998-11-12 | 2003-02-06 | Deyn Wolfgang Von | Process and novel intermediates for preparing isoxazolin-3-ylacyl benzenes |
| CN103788083A (en) * | 2014-03-10 | 2014-05-14 | 中国药科大学 | Method for preparing herbicide topramezone |
| CN108218851A (en) * | 2018-03-09 | 2018-06-29 | 安徽久易农业股份有限公司 | It is a kind of to improve the method for preparing topramezone |
Non-Patent Citations (2)
| Title |
|---|
| The Preparation of o- and p-Nitroacetophenone;A. H. FORD-MOORE，H. N. RYDON;《Journal of the Chemical Society》;19460101;第679-681页 * |
| 农药中间体3-(2-甲基-6-硝基苯基) - 4，5-二氢异恶唑的合成研究;熊国银等;《安徽农业科学》;20131231;第41卷(第34期);第13232－13233页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114163352A (en) | 2022-03-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101417962B (en) | Method for preparing 2-cyano-3-amino acrylic ester derivates | |
| SK16872000A3 (en) | Method for producing isoxazoline-3-yl-acyl benzene | |
| CN114163352B (en) | Preparation method of 2-methyl-6-nitrobenzaldehyde oxime | |
| CN110520410B (en) | Synthesis method of mesotrione | |
| CN109053505B (en) | Synthesis method of important intermediate of feloxicib | |
| SG178239A1 (en) | Process for the preparation of derivatives of 1-(2-halobiphenyl-4-yl)-cyclopropanecarboxylic acid | |
| JP2014133730A (en) | Method for producing 3-aminophenol | |
| CN104402795B (en) | The synthetic method of the formic acid of substituted indole 2 | |
| CN101268044B (en) | Process for the preparation of an epoxy compound and an aldehyde | |
| JP2011168577A (en) | Method for producing 2-amino-4-trifluoromethylpyridines | |
| JP2008542408A (en) | Process for the preparation of substituted azoles | |
| CN107108649A (en) | For the intermediate for preparing the novel method of Thienopyrimidine compound and wherein using | |
| KR20070036080A (en) | Process for producing hydrazone compound | |
| CN101585783B (en) | Preparing method of ortho-nitrobenzonitrile series compound | |
| JP2006131568A (en) | Hydroxynaphthoic acid hydrazide, derivative thereof and method for producing the same | |
| CN112358404A (en) | Preparation method of 2-chloro-6-methylaniline | |
| CN115385832B (en) | Preparation method of 2, 3-dimethyl 4-methylsulfonyl bromobenzene | |
| EP3812368A1 (en) | Method for preparing an n-cyclopropylmethyl aniline compound | |
| BRPI0608383B1 (en) | method for producing a nicotinic acid derivative or salt thereof | |
| CN112939893A (en) | Synthesis method of 4- (4-aminophenyl) -3-morpholinone | |
| CN113845449B (en) | Method for preparing mesotrione herbicide | |
| CN101389602A (en) | Process for preparing 3, 4-disubstituted phenylacetic acids and novel intermediates | |
| US3349111A (en) | Process for the preparation of 3, 5-dibromo-4-hydroxybenzonitrile | |
| CN108484495B (en) | Synthetic method of 3-bromo-7-hydroxyquinoline | |
| JPH0789955A (en) | Production of 2-substituted benzo(b)thiophene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |