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Method for preparing 9-phenylacridine compound

A technology for phenylacridine compounds, which is applied in the field of preparation of 9-phenylacridine compounds, can solve the problems of limiting the application of acridine photoinitiators, low reaction conversion rate, and low crude product content, and facilitates production The effect of selection, high content and short process flow

Pending Publication Date: 2019-11-08
维思普新材料(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in these traditional synthesis methods, there are disadvantages such as high reaction temperature, long time, low reaction conversion rate, low crude product content, repeated refining, and serious environmental pollution, which limit the application of acridine photoinitiators.

Method used

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  • Method for preparing 9-phenylacridine compound
  • Method for preparing 9-phenylacridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In a 250mL three-necked flask, 21.4g (0.1mol) of 9-chloroacridine, 14.6g (0.12mol) of phenylboronic acid, Pd(PPh 3 ) 4 Catalyst 0.11g, toluene 100g, sodium carbonate 2g, deionized water 18g, heated to 40°C, reacted for 3 hours, cooled to 25°C, removed the solvent by rotary evaporation, added 100g methanol to wash and disperse, and suction filtered to obtain the crude product, which was washed with 80g toluene After refining and drying, 24.7 g of the product was obtained, with a yield of 96.8% and an HPLC content of 99.65%. Elemental analysis: Cal: C89.38, H5.13, N5.49 Found: C89.35, H 5.11, N5.48; ESI: 255.31.

Embodiment 2

[0033] In a 250mL three-necked flask, add 21.4g (0.1mol) of 9-chloroacridine, 16.3g (0.12mol) of 3-methylphenylboronic acid, Pd(OAc) 2 Catalyst 0.11g, toluene 100g, sodium carbonate 2g, deionized water 18g, heated to 40°C, reacted for 3 hours, cooled to 25°C, removed the solvent by rotary evaporation, added 100g methanol to wash and disperse, and suction filtered to obtain the crude product, which was washed with 80g toluene Refined and dried to obtain 26.1 g of the product with a yield of 96.9% and an HPLC content of 99.69%. Elemental analysis: Cal: C89.19, H5.61, N5.20 Found: C89.17, H 5.63, N5.21; ESI: 269.33.

Embodiment 3

[0035] In a 250mL three-neck flask, add 21.4g (0.1mol) of 9-chloroacridine, 20.7g (0.14mol) of 3-vinylphenylboronic acid, and PdCl 2 Catalyst 0.12g, toluene 100g, potassium carbonate 2g, deionized water 18g, heated to 50°C, reacted for 4 hours, cooled to 25°C, removed the solvent by rotary evaporation, added 100g methanol to wash and disperse, obtained crude product by suction filtration, and used 80g toluene for the crude product Refined and dried to obtain 27.1 g of the product with a yield of 96.5% and an HPLC content of 99.58%. Elemental analysis: Cal: C89.65, H 5.37, N4.98 Found: C89.64, H 5.35, N4.99; ESI: 281.34.

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Abstract

The invention relates to a method for preparing 9-phenylacridine compound. The method comprises the following steps: reacting a haloacridine compound of formula 1 with phenylboronic acid of formula 2or a derivative thereof in a solvent at 20-80 DEG C in the presence of a palladium catalyst, when the reaction is completed, obtaining 9-phenylacridine compound of formula 3, wherein the solvent comprises an organic solvent and an aqueous solution of a base, X is a first halogen and R is an alkyl group containing 1-18 carbon atoms, an alkenyl group, an alkynyl group, or second halogen. By adoptingthe method of the invention, the reaction conversion rate is above 97%, and the content of the finished product obtained by the post-treatment is above 99%. The process can meet the requirements of industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 9-phenylacridine compounds. Background technique [0002] 9-phenylacridine compounds can be widely used as photoinitiators in photocurable materials (such as photocurable coatings, inks and photoresists) composed of unsaturated resins and monomers thereof. Under ultraviolet light or laser irradiation, These photoinitiators generate active free radicals, thereby initiating polymerization and curing reactions of unsaturated photocurable materials. [0003] Acridine photoinitiators started from Japanese patent JP27605 / 1978, followed by US patent US5334484 / 1994, Green Chemistry Letters and Reviews Vol.4, No.2, June2011, 131-135, GreenChemistry, 2002, 4, 390- 391. Advances in Heterocyclic Chemistry, Volume 115ISSN0065-2725 has been further improved, providing theoretical and practical basis for the development and utilization of acridine photoinitiat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02
CPCC07D219/02
Inventor 陈潇袁晓冬刘海丰于利民陈华
Owner 维思普新材料(苏州)有限公司
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