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Preparation method of acridine compounds

A compound, acridine technology, applied in the new preparation field, can solve the problems of difficult industrialized production, long reaction time, high process cost, achieve mild preparation conditions, avoid high temperature and high pressure reaction and the use of expensive heavy metal catalyst effects

Active Publication Date: 2012-09-19
芜湖启博知识产权运营有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is different from the traditional Berndsen acridine synthesis method, the reaction mechanism is suzuki coupling reaction, but the reaction time is longer, and expensive metal catalysts are used, the process cost is high, and it is difficult to industrialize production

Method used

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  • Preparation method of acridine compounds
  • Preparation method of acridine compounds
  • Preparation method of acridine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of embodiment 1 9-phenylacridine

[0034]

[0035] The first step: the preparation of acridone

[0036] Add 15g of N-phenylanthranilic acid into a 250ml four-necked flask, add 50ml of polyphosphoric acid as a solvent, heat the oil bath to 100°C, and stop the reaction for 3 hours. Slowly add 10% NaHCO dropwise after the reaction solution is cooled 3 PPA was removed from the solution, the reaction solution was adjusted to neutrality, filtered, washed with water and dried to obtain a pale yellow product with a yield of 89.2%. The effect of solvent dosage on the reaction is shown in Table 1.

[0037] Table 1 The influence of solvent consumption on reaction

[0038] experiment

Solvent usage / ml

Yield %

Experiment 1

40

82.9

Experiment 2

50

89.2

Experiment 3

60

88.5

Experiment 4

70

81.3

[0039] The second step: the preparation of 9-hydroxyl-9-phenylacridin...

Embodiment 2

[0046] The preparation of embodiment 2 9-phenylacridine

[0047]

[0048] The first step: the preparation of acridone

[0049] Add 15g of N-phenylanthranilic acid into a 250ml four-neck flask, add 50ml of polyphosphoric acid, heat the oil bath to 100°C, and stop the reaction for 3 hours. Slowly add 10% NaHCO dropwise after the reaction solution is cooled 3 PPA was removed from the solution, the reaction solution was adjusted to neutrality, filtered, washed with water and dried to obtain a pale yellow product with a yield of 89.2%. The effect of different solvents on the reaction is shown in Table 2.

[0050] The impact of different solvents in table 2 on the reaction

[0051] experiment

solvent

Yield %

Experiment 1

concentrated sulfuric acid

81.2

Experiment 2

polyphosphoric acid

89.2

Experiment 3

p-Toluenesulfonic acid

66.5

[0052] The second step: the preparation of 9-hydroxyl-9-phenylacridine...

Embodiment 3

[0059] The preparation of embodiment 3 9-tolyl acridine

[0060]

[0061] The first step: the preparation of acridone

[0062] Add 15g of N-phenylanthranilic acid into a 250ml four-neck flask, add 10ml of water and 20ml of concentrated sulfuric acid mixture, heat the oil bath to 100°C, slowly add 30ml of concentrated sulfuric acid dropwise, and stop stirring after 3 hours of reaction. Slowly add 10% NaHCO dropwise after the reaction solution is cooled 3 The concentrated sulfuric acid was removed from the solution, and the reaction solution was adjusted to be neutral. After filtration, the product was washed with water and dried to obtain a yellow product with a yield of 81.2%. The effect of the amount of concentrated sulfuric acid on the reaction is shown in Table 3.

[0063] The impact of the concentrated sulfuric acid consumption of table 3 on reaction

[0064] experiment

Amount of concentrated sulfuric acid / ml

Yield %

Experiment 1

30

...

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Abstract

The invention provides a preparation method of acridine compounds, and relates to the technical field of photoinitiator. The preparation method comprises the following steps of: taking substituted N-methyl anthranilic acid as initial raw material, generating substituted acridone under the condition of acid, carrying out reaction on substituted bromobenzene and magnesium to generate grignard reagent, carrying out reaction on substituted acridone and the grignard reagent to generate substituted 9-oxhydryl-9-phenylacridine, and reducing to obtain the substituted 9-phenylacridine compounds. Different from the conventional synthesis route, the preparation method of the acridine compounds provided by the invention has more operation steps compared with the conventional one-step method, thus being slightly lower in yield compared with the conventional synthesis route, however, the preparation condition is mild relatively, and the high-temperature and high-pressure reaction and the use of expensive heavy metal catalyst can be avoided, so that the preparation method is good in environment protection.

Description

technical field [0001] The invention relates to the technical field of photoinitiators, in particular to a new preparation method of acridine compounds. Background technique [0002] Acridine compounds are macrocyclic conjugated systems with a rigid planar structure and strong fluorescence properties. They are good fluorescent reagents and can be used as photoinitiators in photopolymerization systems, and can also be used as sensitizers to initiate photoinitiation. agent for photopolymerization. As a photoinitiator, acridine compound is an important part of UV photocuring system. It makes the oligomer and reactive diluent undergo crosslinking and curing reaction rapidly in the formula system under the irradiation of light source, which is the key to the photocuring rate and degree of photocuring. one of the important determinants. As a sensitizer, after absorbing light energy, it can undergo a photophysical process to an excited state of it, and then undergo intramolecular...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D219/06
Inventor 宋国强王道生陈昕于培培金晓蓓
Owner 芜湖启博知识产权运营有限公司
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