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Method for preparing 9,9-dimethyl acridine

A technology of dimethyl acridine and phenyl, which is applied in the field of preparation of 9,9-dimethyl acridine, can solve the problems of complicated steps, the catalyst cannot be reused, etc., and achieves the effect of simple and easy-to-control process and safe operation.

Active Publication Date: 2019-09-17
ZHENGZHOU SIGMA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in the preparation method of this 9,9-dimethylacridine, the steps are complicated, the reaction time is more than 40h, and phosphoric acid is used as the catalyst, and the catalyst cannot be reused

Method used

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  • Method for preparing 9,9-dimethyl acridine
  • Method for preparing 9,9-dimethyl acridine
  • Method for preparing 9,9-dimethyl acridine

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preparation example Construction

[0019] The preparation method of 9,9-dimethylacridine of the present invention comprises the following steps: uniformly mixing 2-(2-(phenylamino)phenyl)propan-2-alcohol and a hydrogen-type molecular sieve catalyst in an organic solvent , react at 20-50°C for 2-4 hours, separate the solid from the liquid, and the resulting solid is 9,9-dimethylacridine. The hydrogen-type molecular sieve is at least one of HM, HY, Hβ, and HZSM-5 molecular sieves. Further preferably, the hydrogen type molecular sieve is HZSM-5.

[0020] In the preparation method of 9,9-dimethylacridine of the present invention, the mass ratio of used 2-(2-(phenylamino)phenyl)propan-2-alcohol, hydrogen type molecular sieve catalyst and organic solvent is 1: (0.01-0.06): (3.3-14).

[0021] The mass ratio of N-phenyl anthranilic acid, Grignard reagent and organic solvent used in the preparation process of 2-(2-(phenylamino) phenyl) propan-2-alcohol of the present invention is 1:(2.3~ 25): (2~10). The organic sol...

Embodiment 1

[0024] The reaction in the preparation process of 9,9-dimethylacridine of the present embodiment is shown in formula (I):

[0025]

[0026] Specifically include the following steps:

[0027] 1) Take N-phenylanthranilic acid (1.06kg, 5mol) in THF (2.4L), replace nitrogen, heat to reflux, add methylmagnesium chloride (32.5mol, 1.68M) dropwise under reflux, add dropwise Continue the reflux reaction for 4 hours after completion, TLC (thin layer chromatography) to determine the reaction end point, after the reaction is completed, cool down to room temperature, slowly add water to quench, control the temperature during the quenching process to be less than 30°C, recover THF under reduced pressure after completion, and cool to room temperature Add 10L of water, adjust the pH to 5-6 with concentrated hydrochloric acid, and dissolve; then extract with 5L of chloroform, repeat the extraction 3 times, then combine the organic phases, remove the water in the organic phase with anhydrou...

Embodiment 2

[0030] The preparation process of the 9,9-dimethylacridine of the present embodiment specifically includes the following steps:

[0031] 1) Take N-phenylanthranilic acid (1.06kg, 5mol) in THF (5.98L), replace nitrogen, heat to reflux, add methylmagnesium chloride (70.83mol, 1.68M) dropwise under reflux, add dropwise Continue the reflux reaction for 6 hours after the completion of the reaction, TLC to determine the end point of the reaction, after the completion of the reaction, cool down to room temperature, slowly add water to quench, control the temperature during the quenching process to be less than 30°C, recover THF under reduced pressure after completion, add 30L of water after cooling to room temperature, and use Adjust the pH to 5-6 with concentrated sulfuric acid, dissolve and clear; then extract with 27L chloroform, repeat the extraction 3 times, then combine the organic phase, remove the moisture in the organic phase with anhydrous sodium sulfate, and spin dry to obt...

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Abstract

The invention belongs to the technical field of organic synthesis and in particular relates to a method for preparing 9,9-dimethyl acridine. The method provided by the invention comprises the following steps: mixing 2-(2-(phenyl amino) phenyl) propane-2-alcohol and a hydrogen type molecular sieve based catalyst in an organic solvent, carrying out a reaction for 2-4 hours at 20-50 DEG C, carrying out solid-liquid separation so as to obtain a liquid phase, and removing the organic solvent in the liquid phase, so as to obtain the 9,9-dimethyl acridine. The method has the advantages of being gentle in reaction condition, simple and convenient in operation, green and environment-friendly and high in product yield and is applicable to large-scale industrial production and application, and the catalyst can be recycled and repeatedly used.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 9,9-dimethylacridine. Background technique [0002] 9,9-Dimethylacridine It is an important intermediate in thermally active delayed fluorescent materials, and has important applications in organic light-emitting diodes. In addition, 9,9-dimethylacridine is also a general-purpose rubber anti-aging agent, which has excellent heat resistance, oxygen resistance, and flex resistance, and also has a certain ability to resist weather and ozone aging. [0003] Although 9,9-dimethylacridine has high application value, most of the existing literature synthesis methods use H 3 PO 4 、H 2 SO 4 As catalysts, the environmental and resource problems caused by the large-scale use of such catalysts are increasingly unacceptable by the development trend of the environmentally friendly chemical industry. Therefore, new catalysts are sought to achi...

Claims

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Application Information

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IPC IPC(8): C07D219/02
CPCC07D219/02Y02P20/584
Inventor 武小军杨勇申丽坤李鹏翔韩学哲
Owner ZHENGZHOU SIGMA CHEM
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