CN113999130A - Preparation method of o-nitroanilide compound - Google Patents
Preparation method of o-nitroanilide compound Download PDFInfo
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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 the acylaniline compound, tert-butyl nitrite and a solvent, and stirring for reaction at 20-60 ℃ 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%.
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
The nitrobenzene compounds are used in the organic synthesis industries of dyes, perfumes, explosives and the like, and are also used in solvents and mild oxidants. The nitro is a strong passivating group, and the nitrobenzene needs to undergo electrophilic substitution reaction under a strong condition to generate a meta-product; has weak oxidation function, can be used as an oxidant for oxidative dehydrogenation, and is prepared by reacting mixed acid of nitric acid and sulfuric acid with benzene. Its main use is in the manufacture of anilines, which are also commonly used as insulating materials and as 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 chlorination of nitrobenzene, is widely used for production of dyes and pesticides, and can be reduced to obtain m-chloroaniline. The product is used as dye orange base GC and is also an intermediate of medicines, pesticides, fluorescent whitening agents, organic pigments and the like. The m-dinitrobenzene can be obtained by re-nitration of nitrobenzene and can be reduced to obtain m-phenylenediamine which can be used as a dye intermediate, an epoxy resin curing agent, a petroleum additive and a cement coagulant, and the m-dinitrobenzene can be partially reduced by sodium sulfide to obtain the m-nitroaniline. Is a dye orange group 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 the problem of how to avoid the use of the oxidant or the catalyst and improve the yield of the compound is the problem in the prior art.
Disclosure of Invention
The invention aims to overcome the technical defects and provide a preparation method of an o-nitroanilide compound. Solves the technical problems of avoiding using a catalyst or an oxidant to prepare the o-nitroanilide compound and improving the yield in the prior art.
In order to achieve the technical purpose, the technical scheme of the invention provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
mixing the acylaniline compound, tert-butyl nitrite and a solvent, and stirring for reaction at 20-60 ℃ to obtain the o-nitroanilide compound.
Further, the stirring reaction time is 3-5 h.
Further, the solvent is hexafluoroisopropanol.
Further, the speed of the stirring reaction is 500-800 r/min.
Further, the method also comprises the following steps of purifying the prepared o-nitroanilide compound: and adding water into the prepared o-nitroanilide compound for mixing, adding ethyl acetate for extraction, then carrying out reduced pressure distillation, and then carrying out column chromatography separation and purification.
Further, the anilide compound is one or more of p-chloroacetanilide, p-methylacetanilide, p-fluoroacetanilide, p-acetoxyacetanilide, p-nitroacetanilide 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.
Furthermore, 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:10 mL.
Compared with the prior art, the invention has the beneficial effects that: the o-nitroanilide compound is obtained by mixing an acylaniline compound, tert-butyl nitrite and a solvent, stirring and reacting at 20-60 ℃ to obtain the o-nitroanilide compound, wherein amide in the acylaniline compound is an activated positioning group, nitration reaction is carried out at the ortho position of phenyl to synthesize the o-nitroacetanilide compound, the tert-butyl nitrite is used as a nitration raw material, the reaction condition is mild, a catalyst or an oxidant is not required, and the obtained o-nitroanilide compound has high yield which can reach 93%.
Drawings
FIG. 1 shows a process for producing a 2-nitro-4-chloroacetanilide compound obtained in example 1 of the present invention1And H, spectrum.
FIG. 2 shows a process for producing a 2-nitro-4-chloroacetanilide compound obtained in example 1 of the present invention13And C, spectrum.
FIG. 3 shows the preparation of 2-nitro-4-methylacetanilide compounds obtained in example 2 of the present invention1H, spectrogram;
FIG. 4 shows a process for producing a 2-nitro-4-methylacetanilide compound obtained in example 2 of the present invention13And C, spectrum.
FIG. 5 shows the preparation of 2-nitro-4-fluoroacetanilide compounds obtained in example 3 of the present invention1H, spectrogram;
FIG. 6 shows the preparation of 2-nitro-4-fluoroacetanilide compounds obtained in example 3 of the present invention13And C, spectrum.
FIG. 7 shows the preparation of 2-nitro-4-acetoxyacetanilide compound prepared in example 4 of the present invention1H, spectrogram;
FIG. 8 shows the preparation of 2-nitro-4-acetoxyacetanilide compound prepared in example 4 of the present invention13And C, spectrum.
FIG. 9 shows the preparation of 2, 4-dinitroacetanilide compound obtained in example 5 of the present invention1H, spectrogram;
FIG. 10 shows the preparation of 2, 4-dinitroacetanilide compound obtained in example 5 of the present invention13And C, spectrum.
Detailed Description
The specific embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
according to the molar ratio of the acylaniline compound to the nitroso-tert-butyl ester of 1:2-3 and the material ratio of the acylaniline compound to the solvent of 1mol (10-30) mL, mixing the acylaniline compound, the nitroso-tert-butyl ester and the solvent hexafluoroisopropanol, and stirring and reacting at the temperature of 20-60 ℃ for 3-5h to obtain the o-nitroanilide compound; further, the speed of the stirring reaction is 500-800 r/min.
The specific embodiment further comprises the step of further purifying the prepared o-nitroanilide compound, specifically, the method comprises the steps of adding water into 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 nitroso-tert-butyl ester is preferably 1:3, and the material ratio of the anilide compound to the solvent is preferably 1mol:10 mL.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The anilide compounds used in the following examples had a purity of 98%, tert-butyl nitrite 90% and hexafluoroisopropanol 99.5%.
Example 1
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
sequentially adding 0.2mmol of p-chloroacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of solvent hexafluoroisopropanol and a No. 5 reaction magneton into a reactor for mixing, introducing condensed water into a condenser tube from bottom to top, and stirring the reactor for reacting for 4 hours at 25 ℃ to obtain a reaction solution containing the 2-nitro-4-chloroacetanilide compound; further, the speed of the stirring reaction was 500 rpm.
This example also includes further purification of the 2-nitro-4-chloroacetanilide compound: pouring the reaction liquid containing the 2-nitro-4-chloroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the 2-nitro-4-chloroacetanilide compound with the yield of 93%.
The structural formula of the 2-nitro-4-chloroacetanilide compound is as follows:
the product was structurally determined via nuclear magnetic resonance hydrogen and carbon spectra:
1H NMR(400MHz,CDCl3):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)；13C NMR(100MHz,CDCl3):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:
sequentially adding 0.2mmol of p-methylacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 reaction magneton into a reactor for mixing, introducing condensed water into a condenser tube from bottom to top, and stirring for reacting for 4 hours at 25 ℃ to obtain a reaction solution containing the 2-nitro-4-methylacetanilide compound; further, the speed of the stirring reaction was 500 rpm.
This example also includes further purification of the 2-nitro-4-methylacetanilide compound: pouring the reaction liquid containing the 2-nitro-4-methylacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification 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 structurally determined via nuclear magnetic resonance hydrogen and carbon spectra:
1H NMR(400MHz,CDCl3):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)；13C NMR(100MHz,CDCl3):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:
sequentially adding 0.2mmol of p-fluoroacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 magneton into a reactor for mixing, introducing condensed water into a condenser tube from bottom to top, and then stirring and reacting for 4 hours at 25 ℃ to obtain a reaction solution containing the 2-nitro-4-fluoroacetanilide compound; further, the speed of the stirring reaction was 500 rpm.
This example also includes further purification of the 2-nitro-4-fluoroacetanilide compound: pouring the reaction liquid containing the 2-nitro-4-fluoroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the 2-nitro-4-fluoroacetanilide compound with the yield of 58%.
The structural formula of the 2-nitro-4-fluoroacetanilide is as follows:
the product was structurally determined via nuclear magnetic resonance hydrogen and carbon spectra:
1H NMR(400MHz,CDCl3):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)；13C NMR(100MHz,CDCl3):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:
sequentially adding 0.2mmol of p-acetoxy acetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 magneton into a reactor for mixing, introducing condensed water into a condenser tube from bottom to top, and stirring for reacting for 4 hours at 25 ℃ to obtain a reaction solution containing a 2-nitro-4-acetoxy acetanilide compound; further, the speed of the stirring reaction was 500 rpm.
This example also includes further purification of the 2-nitro-4-acetoxyacetanilide compound: pouring the reaction liquid containing the 2-nitro-4-acetoxy acetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification 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 structurally determined via nuclear magnetic resonance hydrogen and carbon spectra:
1H NMR(400MHz,CDCl3):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)；13C NMR(100MHz,CDCl3):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:
sequentially adding 0.2mmol of p-nitroacetanilide, 0.6mmol of tert-butyl nitrite, 2mL of hexafluoroisopropanol and a No. 5 magneton into a reactor for mixing, introducing condensed water into a condenser tube from bottom to top, and stirring for reacting for 4 hours at 25 ℃ to obtain a reaction solution containing the 2, 4-dinitroacetanilide compound; further, the speed of the stirring reaction was 500 rpm.
This example also includes further purification of the 2, 4-dinitroacetanilide compound: pouring the reaction liquid containing the 2, 4-dinitroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the 2, 4-dinitroacetanilide compound, wherein the yield is 46%.
The structural formula of the 2, 4-dinitroacetanilide compound is as follows:
the product was structurally determined via nuclear magnetic resonance hydrogen and carbon spectra:
1H NMR(400MHz,CDCl3):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)；13C NMR(100 MHz,CDCl3):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 magneton into a reactor in sequence for mixing, introducing condensed water into a condenser tube from bottom to top, and stirring for reacting for 4 hours at 25 ℃ to obtain a reaction solution containing the 2-nitro-3-chloro-4-methylacetanilide compound; further, the speed of the stirring reaction was 500 rpm.
This example also includes further purification of the 2-nitro-3-chloro-4-methylacetanilide compound: pouring the reaction liquid containing the 2-nitro-3-chloro-4-methylacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the 2-nitro-3-chloro-4-methylacetanilide compound, wherein the yield is 46%.
The structural formula of the 2-nitro-3-chloro-4-methylacetanilide is as follows:
the product was structurally determined via nuclear magnetic resonance hydrogen and carbon spectra:
1H NMR(400 MHz,CDCl3):δ2.27(s,3H),2.37(s,3H),8.06(s,1H),8.84(s,1H),10.26(s,1H)；13C NMR(100 MHz,CDCl3):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:
sequentially adding 0.2mmol of p-chloroacetanilide, 0.4mmol of tert-butyl nitrite, 4mL of solvent hexafluoroisopropanol and a No. 5 reaction magneton into a reactor for mixing, introducing condensed water into a condenser tube from bottom to top, and stirring the reactor for reacting for 3 hours at 60 ℃ to obtain a reaction solution containing the 2-nitro-4-chloroacetanilide compound; further, the speed of the stirring reaction is 800 revolutions per minute.
This example also includes further purification of the 2-nitro-4-chloroacetanilide compound: pouring the reaction liquid containing the 2-nitro-4-chloroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the 2-nitro-4-chloroacetanilide compound with the yield of 89%.
Example 8
The embodiment provides a preparation method of an o-nitroanilide compound, which comprises the following steps:
sequentially adding 0.2mmol of p-chloroacetanilide, 0.5mmol of tert-butyl nitrite, 6mL of solvent hexafluoroisopropanol and a No. 5 reaction magneton into a reactor for mixing, introducing condensed water into a condenser tube from bottom to top, and stirring the reactor for reacting for 5 hours at 40 ℃ to obtain a reaction solution containing the 2-nitro-4-chloroacetanilide compound; further, the speed of the stirring reaction was 700 rpm.
This example also includes further purification of the 2-nitro-4-chloroacetanilide compound: pouring the reaction liquid containing the 2-nitro-4-chloroacetanilide compound into a separating funnel, adding 15mL of distilled water, extracting for 3 times by using 10mL of ethyl acetate, carrying out reduced pressure distillation on an organic phase to obtain a crude product, and carrying out column chromatography separation and purification to obtain the 2-nitro-4-chloroacetanilide compound with the yield of 91%.
The preparation method provided by the invention is environment-friendly, and the synthesized o-nitroacetanilide compound has certain bioactivity through detection in an 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 should not be construed as limiting the scope of the present invention. Any other corresponding changes and modifications made according to the technical idea of the present invention should be included in the protection scope of the claims of the present invention.
Claims (10)
1. The preparation method of the o-nitroanilide compound is characterized by comprising the following steps:
mixing the acylaniline compound, tert-butyl nitrite and a solvent, and stirring for reaction at 20-60 ℃ to obtain the o-nitroanilide compound.
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 solvent is hexafluoroisopropanol.
4. The method for preparing an o-nitroanilide compound according to claim 1, wherein the stirring reaction is carried out at a speed of 500-800 rpm.
5. The method for producing an o-nitroanilide compound according to claim 1, further comprising purifying the produced o-nitroanilide compound: and adding water into the prepared o-nitroanilide compound for mixing, adding ethyl acetate for extraction, then carrying out reduced pressure distillation, and then carrying out column chromatography separation and purification.
6. The method for producing an o-nitroanilide compound according to claim 1, wherein the anilide compound is one or more of p-chloroacetanilide, p-methylacetanilide, p-fluoroacetanilide, p-acetoxyacetanilide, p-nitroacetanilide, and 3-chloro-4-methylacetanilide.
7. The method for producing an o-nitroanilide compound according to claim 1, wherein the molar ratio of the anilide compound to the tert-butyl nitroso ester is 1:2 to 3.
8. The method for producing an o-nitroanilide compound according to claim 7, wherein the molar ratio of the anilide compound to the tert-butyl nitroso ester is 1: 3.
9. The method for preparing an o-nitroanilide compound according to claim 1, wherein the material ratio of the anilide compound to the solvent is 1mol (10-30) mL.
10. The method for producing an o-nitroanilide compound according to claim 9, wherein the material ratio of the anilide compound to the solvent is 1mol:10 mL.
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