CN101823992A - Preparation method of 4-nitroindole - Google Patents
Preparation method of 4-nitroindole Download PDFInfo
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- CN101823992A CN101823992A CN 201010145377 CN201010145377A CN101823992A CN 101823992 A CN101823992 A CN 101823992A CN 201010145377 CN201010145377 CN 201010145377 CN 201010145377 A CN201010145377 A CN 201010145377A CN 101823992 A CN101823992 A CN 101823992A
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- nitroindoline
- methyl
- preparation
- nitro benzene
- consumption
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Abstract
The invention relates to a preparation method of 4-nitroindole. The method comprises the following steps of: adding 2-methyl-3-nitrobenzene, triethyl orthoformate and oxalic acid into a flask by a certain proportion; heating and refluxing to react for certain time and then cooling to 0-10 DEG C; slowly dropping an alcohol solution of potassium ethoxide; continuing to reacting for a period of time at normal temperature and pouring the reaction liquid into ice water to ensure that a large quantity of solid appears; and sucking and filtering to obtain solid, i.e. the 4-nitroindole. The method has the characteristics of high yield, easy operation, and the like.
Description
Technical field
The present invention relates to a kind of preparation method of 4-nitroindoline.
Background technology
The 4-nitroindoline is an important intermediate of producing other simple 4-substituted indoles, also is the important source material of synthetic dyestuff and medicine.Synthetic method foreign study about-nitroindoline is many: become the 4-nitroindoline as closing cyclization by 2-methyl-3-nitro aniline, produce the 4-nitroindoline by m-nitro hydrazone cyclisation posthydrolysis, produce the 4-nitroindoline by the Meta-dinitrobenzene derivative, produce 4-nitroindoline etc. by 4-nitroindoline quinoline.What have value in the method for above-mentioned synthetic 4-nitroindoline is that 2-base-3-N-methyl-p-nitroaniline is a starting raw material, induces by alkali under the promotion of dialkyl group oxalate and produces the 4-nitroindoline.This method raw material is bulk product, and reactions steps is few, and is simple to operate, mild condition, and total recovery is than higher.The raw material costliness that other several methods have, the processing condition of the requirement that has are higher, and the byproduct of reaction that has is more, and is not easily separated.But report too simple.This patent is optimized this reaction on this method research basis, obtains result preferably.
Summary of the invention
The purpose of this invention is to provide a kind of raw material and be easy to get, cost is low, the preparation method of the 4-nitroindoline of the few and mild condition of reactions steps.
For achieving the above object, the present invention adopts following technical scheme to realize:
The preparation method of 4-nitroindoline is characterized in that, may further comprise the steps:
2-methyl-3-nitro benzene, triethyl orthoformate, oxalic acid are added by a certain percentage, certain 2～4 hours of heating reflux reaction, be cooled to 0～10 ℃, slowly drip the ethanolic soln of potassium ethylate, continue reaction 2～4 hours at normal temperatures, reaction solution is poured in the frozen water, a large amount of solids occur, suction filtration obtains solid, is the 4-nitroindoline.
Described triethyl orthoformate consumption is 1～2.5 times of 2-methyl-3-nitro benzene mole number.
Described consumption of oxalic acid is 1～1.5 times of 2-methyl-3-nitro benzene mole number.
Described potassium ethylate consumption is 0.8～1.5 times of 2-methyl-3-nitro benzene mole number;
Described ethanol consumption is 1～1.5 times of 2-methyl-3-nitro benzene mole number.
Advantage of the present invention is as follows:
1,2-methyl-3-nitro benzene, triethyl orthoformate, oxalic acid all are common raw materials, so raw material is easy to get and cost is low.
2, the reaction times short, and reaction temperature and, the safety coefficient height.
3, transformation efficiency height.
4, technology is simple, and is easy to operate.
Embodiment
Embodiment 1
In flask, 2-methyl-3-nitro benzene 76g, triethyl orthoformate 89g, oxalic acid 50g are added, behind the heating reflux reaction 2 hours, be cooled to 10 ℃ after, slowly drip the ethanolic soln 65g of potassium ethylate (42g), continue reaction at normal temperatures after 4 hours, reaction solution is poured in the frozen water, a large amount of solids occurred, suction filtration obtains solid 60g, be the 4-nitroindoline, yield 74%.
Embodiment 2
In flask, 2-methyl-3-nitro benzene 76g, triethyl orthoformate 115g, oxalic acid 70g are added, behind the heating reflux reaction 4 hours, be cooled to 10 ℃ after, slowly drip the ethanolic soln 80g of potassium ethylate (51g), continue reaction at normal temperatures after 4 hours, reaction solution is poured in the frozen water, a large amount of solids occurred, suction filtration obtains solid 66g, be the 4-nitroindoline, yield 81.4%.
Claims (5)
1.4-the preparation method of nitroindoline is characterized in that, may further comprise the steps:
2-methyl-3-nitro benzene, triethyl orthoformate, oxalic acid are added by a certain percentage, certain 2～4 hours of heating reflux reaction, be cooled to 0～10 ℃, slowly drip the ethanolic soln of potassium ethylate, continue reaction 2～4 hours at normal temperatures, reaction solution is poured in the frozen water, a large amount of solids occur, suction filtration obtains solid, is the 4-nitroindoline.
2. according to the preparation of claims 1 described 4-nitroindoline, it is characterized in that: described triethyl orthoformate consumption is 1～2.5 times of 2-methyl-3-nitro benzene mole number.
3. according to the preparation of claims 1 described 4-nitroindoline, it is characterized in that: described consumption of oxalic acid is 1～1.5 times of 2-methyl-3-nitro benzene mole number.
4. according to the preparation of claims 1 described 4-nitroindoline, it is characterized in that: described potassium ethylate consumption is 0.8～1.5 times of 2-methyl-3-nitro benzene mole number.
5. according to the preparation of claims 1 described 4-nitroindoline, it is characterized in that: described ethanol consumption is 1～1.5 times of 2-methyl-3-nitro benzene mole number.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010145377 CN101823992A (en) | 2010-04-01 | 2010-04-01 | Preparation method of 4-nitroindole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010145377 CN101823992A (en) | 2010-04-01 | 2010-04-01 | Preparation method of 4-nitroindole |
Publications (1)
| Publication Number | Publication Date |
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| CN101823992A true CN101823992A (en) | 2010-09-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 201010145377 Pending CN101823992A (en) | 2010-04-01 | 2010-04-01 | Preparation method of 4-nitroindole |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105622483A (en) * | 2016-03-01 | 2016-06-01 | 苏州艾缇克药物化学有限公司 | Synthesis method of 4-nitroindole |
| CN105622484A (en) * | 2016-04-05 | 2016-06-01 | 叶芳 | 4-nitroindole and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481330A (en) * | 2009-01-20 | 2009-07-15 | 常州市阳光医药原料有限公司 | Preparation of N-(4-ethoxy carbonyl phenyl)-N'-methyl-N'-phenyl formamidine |
-
2010
- 2010-04-01 CN CN 201010145377 patent/CN101823992A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481330A (en) * | 2009-01-20 | 2009-07-15 | 常州市阳光医药原料有限公司 | Preparation of N-(4-ethoxy carbonyl phenyl)-N'-methyl-N'-phenyl formamidine |
Non-Patent Citations (3)
| Title |
|---|
| 《Tetrahedron Letters》 19831231 Jan Bergman,et al., A new versatile synthesis of 4-nitroindoles 3665-3668 1-5 第24卷, 第34期 2 * |
| 《Tetrahedron》 19901231 Jan Bergman,et al., Synthesis of Indoles via Ring Closure of 2-Alkylnitroaniline Derivatives 6085-6112 1-5 第46卷, 第17期 2 * |
| 《科学技术与工程》 20090131 何光洪 4-硝基吲哚的合成研究 295-298,305 1-5 第9卷, 第2期 2 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105622483A (en) * | 2016-03-01 | 2016-06-01 | 苏州艾缇克药物化学有限公司 | Synthesis method of 4-nitroindole |
| CN105622483B (en) * | 2016-03-01 | 2019-04-26 | 苏州艾缇克药物化学有限公司 | A kind of synthetic method of 4- nitroindoline |
| CN105622484A (en) * | 2016-04-05 | 2016-06-01 | 叶芳 | 4-nitroindole and preparation method thereof |
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Open date: 20100908 |