Synthesis method of 2, 9-substituted 4-halogenated-1, 10-phenanthroline

A technology of o-phenanthroline and its synthesis method, which is applied in the field of synthesis of 4-halogenated-1,10-phenanthroline, which can solve the problems of low conversion rate, difficulty in purification, unfavorable industrial production, etc., so as to improve the conversion rate , improve the yield, and benefit the effect of industrialized production

Inactive Publication Date: 2020-05-01
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the problems that the above method is difficult to purify, the conversion rate is low, and it is not conducive to industrial production, the present invention discloses a synthesis method of 2,9-substituted 4-halo-1,10-phenanthroline

Method used

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  • Synthesis method of 2, 9-substituted 4-halogenated-1, 10-phenanthroline
  • Synthesis method of 2, 9-substituted 4-halogenated-1, 10-phenanthroline
  • Synthesis method of 2, 9-substituted 4-halogenated-1, 10-phenanthroline

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Embodiment 1

[0027] A kind of synthetic method of 4-chloro-2,9-dimethyl-1,10-phenanthroline, comprising the following steps:

[0028] first step:

[0029]

[0030] Under argon protection, add 273.41 g of trimethyl orthoacetate and 163.99 g of Michaelis acid to a 1L three-necked flask equipped with a mechanical stirrer, a thermometer, a condenser tube, a water separator, and a drying tube, start stirring and heating, and heat up (0.5 h) After reflux reaction at 78°C for 2 hours (75ml of low-boiling point by-products are fractionated while reacting), turn off the heating and cool down to 55°C for use;

[0031] Step two:

[0032]

[0033] Add 60.00 g of 2-methyl-8-aminoquinoline to the reaction solution in the first step, control the temperature at 60°C for 3 hours to stop the reaction, cool the reaction solution to 35°C for 30 minutes, and then filter to obtain a filter cake The crude yellow solid was beaten with 120.00g trimethyl orthoacetate at 35°C for 10min, filtered, and the fil...

Embodiment 2

[0041] A kind of synthetic method of 4-bromo-2,9-dimethyl-1,10-phenanthroline, comprising the following steps:

[0042] first step:

[0043]

[0044] Under argon protection, add 546.82 g of trimethyl orthoacetate and 163.99 g of Michaelis acid to a 1L three-necked flask equipped with a mechanical stirrer, a thermometer, a condenser tube, a water separator, and a drying tube, start stirring and heating, and heat up (0.5 h) After reflux reaction at 98°C for 4 hours (83ml of low-boiling point by-products are fractionated while reacting), turn off the heating and cool down to 65°C for use;

[0045] Step two:

[0046]

[0047]Add 30.00 g of 2-methyl-8-aminoquinoline to the reaction solution in the first step, and react at a temperature of 40°C for 5 hours to stop the reaction; cool the reaction solution to 25°C and keep stirring for 30 minutes, then filter to obtain a filter cake The crude yellow solid was beaten with 60.00g trimethyl orthoacetate at 25°C for 10min, filtere...

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Abstract

The invention discloses a synthesis method of 2, 9-substituted 4-halogenated-1, 10-phenanthroline, and belongs to the technical field of organic synthesis. The synthesis method comprises the followingsteps: S1, coupling mimic acid and trimethyl orthoformate to form alkene; S2, reacting a 8-aminoquinoline derivative with an intermediate alkene in the first step to generate secondary amine; S3, allowing secondary amine to be subjected to intramolecular cyclization to prepare a phenanthroline derivative of 4-keto carbonyl; and S4, synthesizing 4-halogenated-1, 10-phenanthroline of which the 2, 9positions are substituted through halogenation of phosphorus oxyhalide. According to the method, a four-step synthesis method is adopted, all the raw materials are strictly fed in sequence, corresponding purification treatment is carried out after each step of reaction, the conversion rate of each step of reaction is increased, finally, the yield of the product is effectively increased, and the problems that an existing synthesis method is difficult to synthesize and purify through adoption of a one-pot method, and the yield is low are solved; and the purification process is simple, generation of a large amount of waste acid is avoided, environment friendliness is achieved, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing 2,9-substituted 4-halo-1,10-phenanthroline. Background technique [0002] The 2,9-substituted 1,10-phenanthroline compound is an important OLED intermediate, and the currently reported synthesis method is as follows: [0003] Intermediate 2 (Angewandte Chemie International Edition 56.38 (2017): 11365-11369.) was prepared by continuous casting method using Michaelis acid, 8-aminoquinoline derivatives, etc. as raw materials, and then POCl 3 (or POBr 3 ) is that the ketone carbonyl is converted into Cl (or Br) as a solvent, and the synthesis process is as follows: [0004] [0005] This method has a wide scope of application, but in the first step, a large amount of tar is produced in the process of one-pot synthesis of intermediate 2 by continuous casting method, which can only be purified by column chromatography, which is diffic...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 崔春霖贾小伟毛涛王小伟
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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