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Preparation method for 3-nitropyrrole

A technology of nitropyrrole and pyrrole, which is applied in the field of preparation of 3-nitropyrrole, can solve the problems of dangerous use, many reaction steps, and low comprehensive yield, and achieves cheap price, mild reaction conditions, reduced pollution and production cost Effect

Active Publication Date: 2019-03-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the preparation technology of existing 3-nitropyrrole, there are the defects of using dangerous reagents (strongly irritating acid chloride and strong oxidizing nitric acid), many reaction steps (3 to 4 steps), and low comprehensive yield; therefore looking for a It is necessary to prepare a 3-nitropyrrole with mild reaction conditions, good universality, and meeting the requirements of green production

Method used

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  • Preparation method for 3-nitropyrrole
  • Preparation method for 3-nitropyrrole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Taking pyrrole as raw material, its reaction steps are as follows:

[0025] Add pyrrole (0.7 g, 10 mmol), sodium nitrite (1.4 g, 20 mmol), potassium peroxodisulfate (2.7 g, 10 mmol) and acetonitrile (50 ml) into the reaction flask, and react at 60°C;

[0026] TLC tracking reaction until complete completion;

[0027] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain the target product (95% yield). The analytical data of the product are as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 11.56 (s, 1H), 10.64 (s, 1H), 7.20 (dd, J = 5.8, 1.3Hz, 1H), 6.36 (dd, J = 5.8, 1.4Hz, 1H).

Embodiment 2

[0029] Taking pyrrole as raw material, its reaction steps are as follows:

[0030] Add pyrrole (0.7 g, 10 mmol), sodium nitrite (2.1 g, 30 mmol), sodium peroxodisulfate (2.379 g, 10 mmol) and tetrahydrofuran (50 ml) into the reaction flask, and react at 60°C;

[0031] TLC tracking reaction until complete completion;

[0032] The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate=4:1) to obtain the target product (yield 98%).

Embodiment 3

[0034] Taking pyrrole as raw material, its reaction steps are as follows:

[0035] Add pyrrole (0.7 g, 10 mmol), sodium nitrite (1.4 g, 20 mmol), ammonium peroxodisulfate (2.279 g, 10 mmol), and 1,2-dichloroethane (50 mL) into a reaction flask, Reaction at 70°C;

[0036] TLC tracking reaction until complete completion;

[0037] The crude product obtained after the reaction was separated by column chromatography (petroleum ether:ethyl acetate=4:1) to obtain the target product (yield 96%).

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Abstract

The invention discloses a preparation method for 3-nitropyrrole. According to the invention, 3-nitropyrrole is acquired in the manner of adding pyrrole, sodium nitrite and persulfacte into a solvent and reacting at 60-120 DEG C. According to the invention, pyrrole is taken as an initiator; raw materials are easily acquired; the prepared target product can be directly used and also can be used forfurther reaction. According to the invention, sodium nitrite is taken as a nitration reagent, so that use is safe, cost is low, pollution and production cost can be reduced and requirement for green production can be met. The preparation method disclosed by the invention has the advantages of mild reaction conditions, simple reaction operation and after-treatment process, stable and controllable reaction process, high yield of products and suitability for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of 3-nitropyrrole. Background technique [0002] Pyrrole and its derivatives are not only used in the synthesis of drugs, but also important synthetic intermediates of pesticides, spices, dyes and functional materials (Reference 1: M. Zhang, X. Fang, H. Neumann et al., General andregioselective synthesis of pyrroles via ruthenium-catalyzed multicomponent reactions, J. Am. Chem. Soc. 2013, 135, 11384−11388). [0003] 3-Nitropyrrole is an important pyrrole derivative that plays an important role as an alkaloid in the study of DNA (Reference 2: D. Loakes, D. M. Brown, S. Linde et al., 3-Nitropyrrole and 5 -nitroindole as universal bases in primers for DNA sequencing and PCR, Nucleic acids research, 1995, 23, 2361-2366. Reference 3: D. Loakes, Survey and summary: The applications of universal DNA base analogues, Nucleic Acids...

Claims

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Application Information

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IPC IPC(8): C07D207/42
CPCC07D207/42
Inventor 邹建平陶泽坤李成坤达莫拉·苏布
Owner SUZHOU UNIV
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