Method for synthesizing 6-bromomethyl-3-methoxy-2-nitropyridine

A technology of nitropyridine and methoxy, applied in the field of synthesizing 6-bromomethyl-3-methoxy-2-nitropyridine, which can solve the problems of difficult reaction temperature and difficult industrial production

Inactive Publication Date: 2018-10-12
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are few methods on how to synthesize 6-bromomethyl-3-methoxy-2-nitropyridine, and the general synthesis of 6-bromomethyl-3-methoxy-2-nitropyridin

Method used

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  • Method for synthesizing 6-bromomethyl-3-methoxy-2-nitropyridine

Examples

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example 1

[0018] Add 15.4g of 6-methyl-3-hydroxy-2-nitropyridine, 16.5g of magnesium iodide and 100g of water into a 250mL four-necked bottle, heat the water bath to 75°C, add dropwise 14.5g of dimethyl sulfate to react 18 hours; add 200mL ethyl acetate for extraction, separate the water layer, evaporate the ethyl acetate, and recrystallize from ethanol to obtain 16.1 g of 6-methyl-3-methoxy-2-nitropyridine. Add 10.1g of 6-methyl-3-methoxy-2-nitropyridine, 10.3g of sodium bromide and 100mL of carbon tetrachloride into a 500mL four-necked bottle, heat to reflux, add 11g of hydrogen peroxide dropwise, and dropwise add Then continue to react for 36 hours; after the reaction, add 100mL of 1M sodium hydroxide solution, cool, add 200mL of ethyl acetate for extraction, and distill off the ethyl acetate to obtain a yellow oil; the yellow oil is separated by alumina column chromatography, and then 75 % acetonitrile aqueous solution to obtain 11.1 g of light yellow 6-bromomethyl-3-methoxy-2-nitro...

example 2

[0020] Add 15.4g of 6-methyl-3-hydroxy-2-nitropyridine, 16.5g of magnesium iodide and 100g of water into a 250mL four-necked bottle, heat the water bath to 75°C, add dropwise 14.5g of dimethyl sulfate to react 20 hours; add 200mL ethyl acetate for extraction, separate the water layer, evaporate the ethyl acetate, and recrystallize from ethanol to obtain 16.1 g of 6-methyl-3-methoxy-2-nitropyridine. Add 10.1g of 6-methyl-3-methoxy-2-nitropyridine, 10.3g of sodium bromide and 100mL of carbon tetrachloride into a 500mL four-necked bottle, heat to reflux, add 11g of hydrogen peroxide dropwise, and dropwise add Then continue to react for 40 hours; after the reaction, add 100mL of 1M sodium hydroxide solution, cool, add 200mL of ethyl acetate for extraction, and distill off the ethyl acetate to obtain a yellow oil; the yellow oil is separated by alumina column chromatography, and then 75 % acetonitrile aqueous solution to obtain 11.1 g of light yellow 6-bromomethyl-3-methoxy-2-nitro...

example 3

[0022] Add 15.4g of 6-methyl-3-hydroxy-2-nitropyridine, 16.5g of magnesium iodide and 100g of water into a 250mL four-necked bottle, heat the water bath to 75°C, add dropwise 14.5g of dimethyl sulfate to react 24 hours; add 200mL ethyl acetate for extraction, separate the water layer, evaporate the ethyl acetate, and recrystallize from ethanol to obtain 16.1 g of 6-methyl-3-methoxy-2-nitropyridine. Add 10.1g of 6-methyl-3-methoxy-2-nitropyridine, 10.3g of sodium bromide and 100mL of carbon tetrachloride into a 500mL four-necked bottle, heat to reflux, add 11g of hydrogen peroxide dropwise, and dropwise add Then continue to react for 48 hours; after the reaction, add 100mL of 1M sodium hydroxide solution, cool, add 200mL of ethyl acetate for extraction, evaporate the ethyl acetate to obtain a yellow oil; the yellow oil is separated by alumina column chromatography, and then 75 % acetonitrile aqueous solution to obtain 11.1 g of light yellow 6-bromomethyl-3-methoxy-2-nitropyridi...

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Abstract

The invention discloses a method for synthesizing 6-bromomethyl-3-methoxy-2-nitropyridine. The method comprises the synthesizing steps: firstly, mixing 6-methyl-3-hydroxyl-2-nitropyridine, magnesium iodide and water, dropwise adding dimethyl sulfate, carrying out a reaction for 24 hours with heating, carrying out extraction with ethyl acetate, and boiling off the ethyl acetate, so as to obtain 6-methyl-3-methoxyl-2-nitropyridine; and adding carbon tetrachloride and sodium bromide, carrying out stirring for dissolving, dropwise adding hydrogen peroxide, carrying out a reaction with heating, boiling off the carbon tetrachloride, adding 200ml of water, carrying out extraction with ethyl acetate, boiling off the ethyl acetate so as to obtain crude 6-bromomethyl-3-methoxyl-2-nitropyridine, carrying out column chromatography separation, and carrying out recrystallization with acetonitrile water, thereby obtaining the 6-bromomethyl-3-methoxy-2-nitropyridine. According to the method, the yieldis 75%.

Description

technical field [0001] The invention relates to a synthesis method, a method for synthesizing 6-bromomethyl-3-methoxy-2-nitropyridine. Background technique [0002] Pyridine organic chemical intermediates can be widely used in pesticides, medicines, dyes, spices, etc. It is an important organic chemical intermediate with a wide range of uses. The new compounds obtained by replacing the benzene ring with pyridine often have higher biological activity or lower toxicity. Therefore, in recent years, people have replaced the benzene ring in the molecular structure of existing varieties with pyridine groups, or added pyridyl groups to existing compounds. Introduce other groups into the molecule of the group for derivatization in order to obtain new active compounds. How to synthesize 6-bromomethyl-3-methoxy-2-nitropyridine is rarely introduced so far, and the general synthesis of 6-bromomethyl-3-methoxy-2-nitropyridine requires toxic Methyl iodide is very expensive, and the reac...

Claims

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Application Information

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IPC IPC(8): C07D213/65
CPCC07D213/65
Inventor 夏天喜林富荣
Owner CHANGZHOU UNIV
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