Synthetic method of 2, 9-dinitro-4, 7-dimethyl-1, 10-phenanthroline

A synthetic method, dimethyl technology, applied in the direction of organic chemistry, etc.

Inactive Publication Date: 2016-02-24
丁玉琴
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Therefore, in recent years, the research on 1,10-phenanthroline and its derivatives has always been a hot spot for chemists. At present, for 2,9-dinitro-4,7-dimethyl-1,10-phenanthroline The synthetic method has not been reported yet. As an important intermediate in organic synthesis, 2,9-dinitro-4,7-dimethyl-1,10-phenanthroline is of great benefit in the fields of medicine and chemical industry. place

Method used

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  • Synthetic method of 2, 9-dinitro-4, 7-dimethyl-1, 10-phenanthroline
  • Synthetic method of 2, 9-dinitro-4, 7-dimethyl-1, 10-phenanthroline

Examples

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Effect test

example 1

[0017] First take 150g of nitrobenzene and 30g of SnCl 2 2H 2 After stirring and mixing, put it in the reactor, fill it with hydrogen and add 2g of iron powder, add 500mL of hydrochloric acid solution with a mass fraction of 60% into the reactor, seal it and raise the temperature to 105°C, the pressure is raised to 2MPa, and stir to reduce 4h, cool down to 40°C and filter, heat and melt the filter cake, distill under reduced pressure, collect the fraction at 180°C to obtain crude aniline, then put it into a container, add absolute ethanol to it, stir until the crude aniline is completely dissolved, and then filter , spray-dry the obtained filtrate to obtain aniline; mix and stir the above-prepared aniline and hydrogen peroxide at a mass ratio of 2:1, and after stirring and mixing evenly, slowly add 20 mL of benzoyl chloride dropwise at a temperature of 10°C , stirred for 45min, while adding mass fraction is 95% ethanol, the volume ratio of the amount added to benzoyl chloride...

example 2

[0019]First take 100g of nitrobenzene and 20g of SnCl 2 2H 2 After stirring and mixing, put it in the reactor, fill it with hydrogen and add 1-2g of iron powder, add 300mL of hydrochloric acid solution with a mass fraction of 60% into the reactor, seal it and heat up to 100°C, and the pressure rises to 1.5MPa , stirred and reduced for 2 hours, cooled to 30°C and filtered, heated and melted the filter cake, distilled under reduced pressure, collected the fraction at 120°C to obtain crude aniline, then put it into a container, added absolute ethanol to it, and stirred until the crude aniline was completely After dissolving, filter, and spray-dry the resulting filtrate to obtain aniline; mix and stir the above-prepared aniline and hydrogen peroxide at a mass ratio of 2:1, and after stirring and mixing evenly, slowly add 10 mL of Benzoyl chloride, stirred for 30 minutes, while adding ethanol with a mass fraction of 95%, the volume ratio of the added amount to benzoyl chloride was...

example 3

[0021] First take 120g of nitrobenzene and 25g of SnCl 2 2H 2 After stirring and mixing, put it in the reactor, fill it with hydrogen and add 1g of iron powder, add 400mL of hydrochloric acid solution with a mass fraction of 60% into the reactor, seal and heat up to 101°C, the pressure is raised to 1.7MPa, and stir Restore for 3 hours, cool down to 35°C and filter, heat and melt the filter cake, distill under reduced pressure, collect fractions at 150°C to obtain crude aniline, then put it into a container, add absolute ethanol to it, and stir until the crude aniline is completely dissolved Filtrate, and spray-dry the resulting filtrate to obtain aniline; mix and stir the above-prepared aniline and hydrogen peroxide at a mass ratio of 2:1, and after stirring and mixing evenly, slowly add 15 mL of benzidine dropwise at a temperature of 7°C Acyl chloride, stirred for 40min, while adding ethanol with a mass fraction of 95%, the volume ratio of the added amount to benzoyl chlorid...

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Abstract

The invention relates to a synthetic method of 2, 9-dinitro-4, 7-dimethyl-1, 10-phenanthroline, and belongs to the technical field of organic chemistry. The method comprises the following steps: stirring and mixing nitrobenzene and SnCl2.2H2O, filling with hydrogen, adding iron powder and hydrochloric acid, reacting under certain conditions to obtain aniline, respectively mixing aniline with hydrogen peroxide and benzoyl chloride and adding ethanol, stirring and heating, adding nitric acid, heating, adding chlorosuccinimide in a dropwise manner, mixing with a hydrochloric acid and water mixed solution, carrying out water bath heating, adding zinc powder, stirring and reacting, adding a sodium hydroxide solution, and distilling the obtained solution to obtain a distillate which is 4-methyl-8-aminoquinoline; and heating 4-methyl-8-aminoquinoline, benzoyl chloride and to reflux, cooling to room temperature, slowly adding nitric acid in a dropwise manner, filtering, mixing the obtained filtrate with stannous chloride, heating, adding zinc powder and hydrochloric acid, and carrying out stirring and pumping filtration, and carrying out vacuum drying to obtain 2, 9-dinitro-4, 7-dimethyl-1, 10-phenanthroline. The method has the advantages of mild reaction conditions, simple operation and low cost.

Description

technical field [0001] The invention relates to a synthesis method of 2,9-dinitro-4,7-dimethyl-1,10-phenanthroline, which belongs to the technical field of organic chemistry. Background technique [0002] Since 1,10-phenanthroline was artificially synthesized, it has been widely used in various fields of chemistry. Its structure is rigid, two nitrogen atoms are in adjacent positions, and the 1,10-phenanthroline ring is also a good π electron acceptor, which can form a feedback π bond when coordinating with metal ions, especially to stabilize the low-valence state It has good coordination ability for transition metal and lanthanide metal ions. Introducing 1,10-phenanthroline into multi-component complexes as a second ligand can not only improve the stability of the complexes, but also obtain novel materials with novel structures and properties. By introducing substituents and functional groups at different positions of 1,10-phenanthroline, changing the coordination structur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 丁玉琴薛红娟
Owner 丁玉琴
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