CN113999130B - Preparation method of o-nitroanilide compound - Google Patents
Preparation method of o-nitroanilide compound Download PDFInfo
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- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Abstract
The invention discloses a preparation method of an o-nitroanilide compound, belonging to the technical field of organic synthesis. The preparation method of the o-nitroanilide compound comprises the following steps: mixing an anilide compound, tert-butyl nitrite and a solvent, and stirring at 20-60 ℃ for reaction to obtain the o-nitroanilide compound. The preparation method does not need a catalyst or an oxidant, and the obtained o-nitroanilide compound has high yield which can reach 93 percent.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of an o-nitroanilide compound.
Background
Nitrobenzene compounds are used in organic synthesis industries such as dyes, fragrances, explosives, and the like, as well as in solvents and mild oxidants. The nitro is Jiang Dunhua, nitrobenzene needs to undergo electrophilic substitution reaction under stronger conditions to generate meta-position products; the mixed acid of nitric acid and sulfuric acid is commonly used as an oxidant for oxidative dehydrogenation and is reacted with benzene to prepare the catalyst. Its main use is to make aniline compounds, also commonly used as insulating materials and gloss agents. Nitrobenzene is an important organic intermediate. And sulfonating nitrobenzene with sulfur trioxide to obtain m-nitrobenzenesulfonic acid. The nitrobenzene is sulfonated by chlorosulfonic acid to obtain m-nitrobenzenesulfonyl chloride which is used as an intermediate of dye, medicine and the like. The m-nitrochlorobenzene is obtained by chloridizing nitrobenzene, and is widely used for the production of dyes and pesticides, and the m-chloroaniline can be obtained after reduction. Used as dye orange chromophore GC and also as an intermediate of medicines, pesticides, fluorescent whitening agents, organic pigments and the like. The m-dinitrobenzene can be obtained by nitrosation of nitrobenzene, and m-phenylenediamine can be obtained by reduction and used as a dye intermediate, an epoxy resin curing agent, a petroleum additive and a cement accelerator, and the m-dinitrobenzene is subjected to partial principle such as sodium sulfide to obtain the m-nitroaniline. The dye orange chromophore R is an intermediate of azo dyes, organic pigments and the like.
In the preparation method of the o-nitroanilide compound, a catalyst or an oxidant is generally required, the yield is low, and how to avoid using the oxidant or the catalyst and improve the yield of the compound is a difficult problem in the prior art.
Disclosure of Invention
The invention aims to overcome the technical defects and provide a preparation method of o-nitroanilide compounds. Solves the technical problems of how to avoid using a catalyst or an oxidant to prepare the o-nitroanilide compound and improve the yield of the o-nitroanilide compound in the prior art.
In order to achieve the technical purpose, the technical scheme of the invention provides a preparation method of o-nitroanilide compounds, which comprises the following steps:
mixing an anilide compound, tert-butyl nitrite and a solvent, and stirring at 20-60 ℃ for reaction to obtain the o-nitroanilide compound.
Further, the stirring reaction time is 3-5h.
Further, the solvent is hexafluoroisopropanol.
Further, the stirring reaction speed is 500-800 rpm.
Further, the method also comprises the step of purifying the prepared o-nitroanilide compound: mixing the prepared o-nitroanilide compound with water, adding ethyl acetate for extraction, performing reduced pressure distillation, and performing column chromatography separation and purification.
Further, the anilide compound is one or more of parachloroacetanilide, paracetamol and 3-chloro-4-methylacetanilide.
Further, the molar ratio of the anilide compound to the nitroso-tert-butyl ester is 1:2-3.
Further, the molar ratio of the anilide compound to the nitroso-tert-butyl ester is 1:3.
Further, the material ratio of the anilide compound to the solvent is 1mol (10-30) mL.
Further, the material ratio of the anilide compound to the solvent is 1mol:10mL.
Compared with the prior art, the invention has the beneficial effects that: mixing an anilide compound, tert-butyl nitrite and a solvent, stirring at 20-60 ℃ for reaction to obtain the o-nitroanilide compound, wherein amide in the anilide compound is an activated positioning group, and performing nitration reaction at the ortho position of phenyl to synthesize the o-nitroanilide compound, wherein tert-butyl nitrite is used as a nitration raw material, the reaction condition is mild, a catalyst or an oxidant is not needed, and the obtained o-nitroanilide compound has high yield which can reach 93%.
Drawings
FIG. 1 is a schematic diagram of a 2-nitro-4-chloroacetanilide compound obtained in example 1 of the present invention 1 H spectrum.
FIG. 2 is a schematic diagram of a 2-nitro-4-chloroacetanilide compound obtained in example 1 of the present invention 13 C spectrogram.
FIG. 3 is a schematic diagram of a 2-nitro-4-methylacetanilide compound obtained in example 2 of the present invention 1 H spectrogram;
FIG. 4 is a schematic diagram of a 2-nitro-4-methylacetanilide compound obtained in example 2 of the present invention 13 C spectrogram.
FIG. 5 is a schematic diagram of a 2-nitro-4-fluoroacetanilide compound obtained in example 3 of the present invention 1 H spectrogram;
FIG. 6 is a schematic diagram of a 2-nitro-4-fluoroacetanilide compound obtained in example 3 of the present invention 13 C spectrogram.
FIG. 7 is a schematic diagram of a 2-nitro-4-acetoxyacetanilide compound according to example 4 of the invention 1 H spectrogram;
FIG. 8 is a schematic diagram of a 2-nitro-4-acetoxyacetanilide compound according to example 4 of the invention 13 C spectrogram.
FIG. 9 is a schematic diagram of a 2, 4-dinitroacetanilide compound obtained in example 5 of the present invention 1 H spectrogram;
FIG. 10 is a schematic diagram of a 2, 4-dinitroacetanilide compound produced in example 5 of the invention 13 C spectrogram.
Detailed Description
The specific embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
mixing an anilide compound, tert-butyl nitrite and hexafluoroisopropanol serving as a solvent according to the molar ratio of the anilide compound to nitroso tert-butyl ester of 1:2-3 and the material ratio of the anilide compound to the solvent of 1mol (10-30) mL, and stirring at 20-60 ℃ for 3-5 hours to obtain the o-nitroanilide compound; further, the stirring reaction speed is 500-800 rpm.
The specific embodiment also comprises further purifying the prepared o-nitroanilide compound, specifically comprising the steps of adding water to the prepared o-nitroanilide compound, mixing, adding ethyl acetate, extracting for 2-3 times, then carrying out reduced pressure distillation, and then carrying out column chromatography separation and purification.
In certain embodiments, the molar ratio of the anilide compound to the nitrosot-butyl ester is preferably 1:3, and the feed ratio of the anilide compound to the solvent is preferably 1mol:10mL.
The present invention will be described in further detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
The anilide compound used in the following examples had a purity of 98%, tert-butyl nitrite had a purity of 90%, and hexafluoroisopropanol had a purity of 99.5%.
Example 1
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of parachloroacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of solvent hexafluoroisopropanol and a No. 5 reaction magnet into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring the reactor at 25 ℃ for 4 hours to obtain a reaction solution containing 2-nitro-4-chloroacetanilide compound; further, the stirring reaction speed was 500 rpm.
This example also includes further purification of the 2-nitro-4-chloroacetanilide compound: pouring the reaction solution containing the 2-nitro-4-chloroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting 3 times with 10mL of ethyl acetate, distilling an organic phase under reduced pressure to obtain a crude product, and separating and purifying by column chromatography to obtain the 2-nitro-4-chloroacetanilide compound, wherein the yield is 93%.
The structural formula of the 2-nitro-4-chloroacetanilide compound is as follows:
the product was structured via nmr hydrogen and carbon spectra:
1 H NMR(400MHz,CDCl 3 ):δ2.28(s,3H),7.58(dd,J＝9.13,2.44Hz,1H),8.17(d,J＝2.46Hz,1H),8.75(d,J＝9.13Hz,1H),10.23(s,1H)； 13 C NMR(100MHz,CDCl 3 ):δ24.2,123.9,125.8,129.0,130.3,135.7,143.8,168.5。
example 2
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of p-methylacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 reaction magnet into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring and reacting for 4 hours at 25 ℃ to obtain a reaction solution containing a 2-nitro-4-methylacetanilide compound; further, the stirring reaction speed was 500 rpm.
This example also includes further purification of the 2-nitro-4-methylacetanilide compound: pouring the reaction solution containing the 2-nitro-4-methylacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting 3 times by using 10mL of ethyl acetate, distilling an organic phase under reduced pressure to obtain a crude product, and separating and purifying by column chromatography to obtain the 2-nitro-4-methylacetanilide compound, wherein the yield is 78%.
The structural formula of the 2-nitro-4-methylacetanilide compound is as follows:
the product was structured via nmr hydrogen and carbon spectra:
1 H NMR(400MHz,CDCl 3 ):δ2.26(s,3H),2.37(s,3H),7.44(d,J＝8.61Hz,1H),7.98(s,1H),8.60(d,J＝8.63Hz,1H),10.18(s,1H)； 13 C NMR(100MHz,CDCl 3 ):δ20.5,25.5,122.1,125.5,132.4,133.5,136.2,136.8,168.9。
example 3
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of p-fluoroacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 magnon into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring at 25 ℃ for 4 hours to obtain a reaction solution containing a 2-nitro-4-fluoroacetanilide compound; further, the stirring reaction speed was 500 rpm.
This example also includes further purification of the 2-nitro-4-fluoroacetanilide compound: pouring the reaction solution containing the 2-nitro-4-fluoroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting 3 times with 10mL of ethyl acetate, distilling an organic phase under reduced pressure to obtain a crude product, and separating and purifying by column chromatography to obtain the 2-nitro-4-fluoroacetanilide compound, wherein the yield is 58%.
The structural formula of the 2-nitro-4-fluoroacetanilide is as follows:
the product was structured via nmr hydrogen and carbon spectra:
1 H NMR(400MHz,CDCl 3 ):δ2.28(s,3H),7.36-7.42(m,1H),7.91(dd,J＝8.48,3.02Hz,1H),8.78(dd,J＝9.42,5.16Hz,1H),10.16(s,1H)； 13 C NMR(100MHz,CDCl 3 ):δ25.5,112.2(d,J＝27.3Hz),123.5(d,J＝22.0Hz),124.1(d,J＝7.3Hz),131.4,155.7,158.2,168.9。
example 4
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of p-acetoxyacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 magnon into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring and reacting for 4 hours at 25 ℃ to obtain a reaction solution containing 2-nitro-4-acetoxyacetanilide compound; further, the stirring reaction speed was 500 rpm.
This example also includes further purification of the 2-nitro-4-acetoxyacetanilide compound: pouring the reaction solution containing the 2-nitro-4-acetoxy acetanilide compound into a separating funnel, adding 15mL of distilled water, extracting 3 times by using 10mL of ethyl acetate, obtaining a crude product by reduced pressure distillation of an organic phase, and separating and purifying by column chromatography to obtain the 2-nitro-4-acetoxy acetanilide compound, wherein the yield is 50%.
The structural formula of the 2-nitro-4-acetoxy acetanilide compound is as follows:
the product was structured via nmr hydrogen and carbon spectra:
1 H NMR(400MHz,CDCl 3 ):δ2.32(s,3H),3.95(s,3H),8.23-8.27(m,1H),8.87(d,J＝1.52Hz,1H),8.90(d,J＝8.94Hz,1H),10.53(s,1H)； 13 C NMR(100MHz,CDCl 3 ):δ25.8,52.6,121.6,124.9,127.5,135.5,136.5,138.3,164.6,169.1。
example 5
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of p-nitroacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 magnon into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring and reacting for 4 hours at 25 ℃ to obtain a reaction solution containing a 2, 4-dinitroacetanilide compound; further, the stirring reaction speed was 500 rpm.
This example also includes the further purification of the 2, 4-dinitroacetanilide compound: pouring the reaction solution containing the 2, 4-dinitroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting 3 times by using 10mL of ethyl acetate, and obtaining a crude product by reduced pressure distillation of an organic phase, wherein the yield of the 2, 4-dinitroacetanilide compound is 46 percent through column chromatography separation and purification.
The structural formula of the 2, 4-dinitroacetanilide compound is as follows:
the product was structured via nmr hydrogen and carbon spectra:
1 H NMR(400MHz,CDCl 3 ):δ2.37(s,3H),8.46-8.49(m,1H),9.09(d,J＝9.42 Hz,1H),9.12-9.14(m,1H),10.64(s,1H)； 13 C NMR(100 MHz,CDCl 3 ):δ25.8,122.0,122.3,130.2,134.9,139.8,141.7,169.3。
example 6
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of 3-chloro-4-methylacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 magnon into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring and reacting for 4 hours at 25 ℃ to obtain a reaction solution containing 2-nitro-3-chloro-4-methylacetanilide compound; further, the stirring reaction speed was 500 rpm.
This example also includes further purification of the 2-nitro-3-chloro-4-methylacetanilide compound: pouring the reaction solution containing the 2-nitro-3-chloro-4-methylacetanilide compound into a separating funnel, adding 15mL distilled water, extracting 3 times by using 10mL ethyl acetate, and obtaining a crude product by vacuum distillation of an organic phase, wherein the yield of the 2-nitro-3-chloro-4-methylacetanilide compound is 46 percent by column chromatography separation and purification.
The structural formula of the 2-nitro-3-chloro-4-methylacetanilide is as follows:
the product was structured via nmr hydrogen and carbon spectra:
1 H NMR(400 MHz,CDCl 3 ):δ2.27(s,3H),2.37(s,3H),8.06(s,1H),8.84(s,1H),10.26(s,1H)； 13 C NMR(100 MHz,CDCl 3 ):δ19.5,25.6,122.1,127.0,131.6,133.4,134.2,142.9,168.9。
example 7
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of parachloroacetanilide, 0.4mmol of tert-butyl nitrite, 4mL of solvent hexafluoroisopropanol and a No. 5 reaction magnet into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring the reactor at 60 ℃ for 3 hours to obtain a reaction solution containing 2-nitro-4-chloroacetanilide compound; further, the stirring reaction speed was 800 rpm.
This example also includes further purification of the 2-nitro-4-chloroacetanilide compound: the reaction solution containing the 2-nitro-4-chloroacetanilide compound is poured into a separating funnel, 15mL of distilled water is added, the mixture is extracted for 3 times by 10mL of ethyl acetate, the organic phase is distilled under reduced pressure to obtain a crude product, and the crude product is separated and purified by column chromatography to obtain the 2-nitro-4-chloroacetanilide compound, wherein the yield is 89%.
Example 8
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
adding 0.2mmol of parachloroacetanilide, 0.5mmol of tert-butyl nitrite, 6mL of solvent hexafluoroisopropanol and a No. 5 reaction magnet into a reactor in sequence, mixing, introducing condensed water into a condensing tube from bottom to top, and stirring the reactor at 40 ℃ for reacting for 5 hours to obtain a reaction solution containing 2-nitro-4-chloroacetanilide compound; further, the stirring reaction speed is 700 revolutions/min.
This example also includes further purification of the 2-nitro-4-chloroacetanilide compound: the reaction solution containing the 2-nitro-4-chloroacetanilide compound is poured into a separating funnel, 15mL of distilled water is added, the mixture is extracted for 3 times by 10mL of ethyl acetate, the organic phase is distilled under reduced pressure to obtain a crude product, and the crude product is separated and purified by column chromatography to obtain the 2-nitro-4-chloroacetanilide compound, wherein the yield is 91%.
The preparation method provided by the invention is environment-friendly, and the detection shows that the synthesized o-nitroacetanilide compound has a certain biological activity in the experimental process, and can be applied to the fields of medicine synthesis, pesticide synthesis, paint dye synthesis and the like.
The above-described embodiments of the present invention do not limit the scope of the present invention. Any other corresponding changes and modifications made in accordance with the technical idea of the present invention shall be included in the scope of the claims of the present invention.
Claims (7)
1. The preparation method of the o-nitroanilide compound is characterized by comprising the following steps of:
mixing an anilide compound, tert-butyl nitrite and a solvent, stirring at 20-60 ℃ for reaction to obtain the o-nitroanilide compound, wherein the solvent is hexafluoroisopropanol, the anilide compound is parachloroacetanilide, and the method further comprises purifying the prepared o-nitroanilide compound: mixing the prepared o-nitroanilide compound with water, adding ethyl acetate for extraction, performing reduced pressure distillation, and performing column chromatography separation and purification.
2. The method for producing an o-nitroanilide compound according to claim 1, wherein the stirring reaction is carried out for 3 to 5 hours.
3. The method for producing an o-nitroanilide compound according to claim 1, wherein the stirring reaction is carried out at a speed of 500 to 800 rpm.
4. The method for producing an o-nitroanilide compound according to claim 1, wherein the molar ratio of the anilide compound to the nitrosot-butyl ester is 1:2-3.
5. The method for producing an o-nitroanilide compound according to claim 4, wherein the molar ratio of the anilide compound to the nitrosot-butyl ester is 1:3.
6. The method for producing an o-nitroanilide compound according to claim 1, wherein the material ratio of the anilide compound to the solvent is 1mol (10-30 mL).
7. The method for producing an o-nitroanilide according to claim 6, wherein the material ratio of the anilide to the solvent is 1 mol/10 mL.
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