Nitration method of quinoxaline substituted alkane

A technology of quinoxaline and alkanes, which is applied in the field of nitration of quinoxaline-substituted alkanes, can solve problems such as limitations, high energy consumption, and difficulty in obtaining high-purity nitroalkanes, and achieves simple operation, high product purity, The effect of strong substrate universality

Active Publication Date: 2014-08-06
临沭县益兴供汽维修服务有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the problem that the current nitration method not only consumes a lot of energy, but also is difficult to obtain high-purity nitroalkane products, thereby limiting its practical application, the present invention provides a nitration method for quinoxaline-substituted alkanes. Selective and relatively mild conditions to obtain the desired nitration products, without the phenomenon of carbon-carbon bond breakage that is prone to occur in traditional methods

Method used

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  • Nitration method of quinoxaline substituted alkane

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Embodiment 1

[0026]

[0027] Add 0.3mmol of 2-isopropylquinoxaline, 0.45mmol of silver nitrite (silver nitrite serves as both a catalyst and a nitro source), and 0.45mmol of potassium persulfate into a 10mL pressure-resistant reactor, and then add 3mL of 1,2- Dichloroethane was used as the reaction solvent. Then magnetic stirring was performed at 3 bar and 110° C. for 48 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the reaction solvent was removed by distillation under reduced pressure, and then the pure product was obtained by column chromatography (based on petroleum ether / ethyl acetate=6: 1 as eluent). The material (2-quinoxalinyl 2-nitropropane) was obtained as a brown oily liquid in 82% yield.

[0028] Characterization data: 1 H NMR (CDCl 3 , 500MHz): δ8.97(s, 1H), 8.16-8.10(m, 2H), 7.84-7.82(m, 2H), 2.19(s, 6H); 13 C NMR (CDCl 3 , 125MHz): δ152.7, 142.3, 142.0, 141.0, 130.8, 130.7, 129.7, 129.2, 90.7, 26.4...

Embodiment 2

[0030]

[0031] Add 0.3mmol of 2-isopropylquinoxaline, 0.06mmol of silver nitrate, 0.45mmol of silver nitrite, and 0.45mmol of potassium persulfate into a 10mL pressure-resistant reactor, and then add 1mL of 1,2-dichloroethane as a reaction solvent. Then magnetic stirring was carried out at 5 bar and 110° C. for 48 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the reaction solvent was removed by distillation under reduced pressure, and then the pure product was obtained by column chromatography (based on petroleum ether / ethyl acetate=6: 1 as eluent). The material (2-quinoxalinyl 2-nitropropane) was obtained as a brown oily liquid in 80% yield.

Embodiment 3

[0033]

[0034] Add 0.3mmol of 2-isopropylquinoxaline, 0.06mmol of silver sulfate, 0.45mmol of silver nitrite, and 0.45mmol of potassium persulfate into a 10mL pressure-resistant reactor, and then add 10mL of 1,2-dichloroethane as a reaction solvent. Then magnetic stirring was performed at 8 bar and 100° C. for 72 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the reaction solvent was removed by distillation under reduced pressure, and then the pure product was obtained by column chromatography (based on petroleum ether / ethyl acetate=6: 1 as eluent). The material (2-quinoxalinyl 2-nitropropane) was obtained as a brown oily liquid in 56% yield.

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Abstract

The invention relates to a synthesis method of an organic compound, and provides a nitration method of quinoxaline substituted alkane in order to solve the problems that a conventional nitration method is high in energy consumption, a high-purity nitro-paraffin product is difficult to obtain and the actual application of the high-purity nitro-paraffin product is limited. The nitration method comprises the steps as follows: 2-quinoxaline substituted alkane, a catalyst, a nitration reagent, an oxidant and a reaction solvent are sequentially added in a sealed pressure-resistant container, a mixture is heated and reacts under the pressure of 1 bar-10 bar for 6-72 hours in oil bath at the temperature of 50 DEG C-150 DEG C, and quinoxaline substituted alkane is obtained. With the adoption of the method, the required nitration product is obtained under the relative mild condition through very high selectivity, and the phenomenon of high probability of carbon-carbon bond rupture witha traditional method is avoided.

Description

technical field [0001] The invention relates to a synthesis method of organic compounds, in particular to a nitration method of quinoxaline-substituted alkanes. Background technique [0002] Nitro compounds are important fine chemical raw materials, widely used in industries such as dyes, medicines, pesticides, chemical fibers, rubber and explosives. In addition, because nitro groups have extremely strong functional group transformation properties, they are considered to be "ideal organic synthesis intermediates" and play a very important role in the field of basic organic synthesis. For example, nitroalkane is a chemical intermediate widely used in the fine chemical industry, and nearly two thousand derivatives can be produced. Nitroalkanes can be converted into nitroso compounds and oxime compounds by catalytic reduction, and oxime compounds can be converted into amides or synthetic pesticides through Beckmann rearrangement reaction; amines can be obtained by completely r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/42
CPCC07D241/42
Inventor 刘运奎张剑崔建海徐振元
Owner 临沭县益兴供汽维修服务有限公司
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