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Preparing method of acridine

A technology of acridine and carboxyl, which is applied in the field of preparation of acridine, can solve the problems of low yield, achieve high purity and yield, good industrial application value, and reduce the effect of industrial manufacturing cost

Active Publication Date: 2019-07-12
ZHENGZHOU SIGMA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The object of the present invention is to provide a kind of preparation method of acridine, to solve the problem that the yield of existing preparation method is low

Method used

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  • Preparing method of acridine

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preparation example Construction

[0018] The preparation method embodiment 1 of acridine of the present invention, synthetic route is as follows:

[0019]

[0020] Specifically adopt the following steps to prepare:

[0021] Add 9-carboxyacridine 3.13kg (14.03mol) in the reactor with thermometer and reflux device, cuprous oxide 0.02kg (0.14mol), o-phenanthroline 0.02kg (0.11mol), NMP (N-methyl pyrrolidone) 4.17kg (42.09mol), reacted at 140°C for 8h, evaporated the NMP solvent after the reaction, added 1.5L of water and mixed evenly, filtered to obtain a black crude product, and recrystallized the black crude product with petroleum ether to obtain acridine The light yellow solid was 2.35kg, the purity was 99.1%, and the yield was 93.0%.

[0022] The NMR H spectrum of the product is as figure 1 and figure 2 Shown, the characteristic data are: HNMR (CDCl 3 , 400Hz) δ: 8.76 (s, 1H); 8.24-8.26, (d, 2H, J=8); 7.98-8.00 (d, 2H, J=8); 7.76-7.79 (m, 2H); 7.51- 7.55 (m, 2H).

Embodiment 2

[0023] The preparation method embodiment 2 of acridine of the present invention, synthetic route is as follows:

[0024]

[0025] Specifically adopt the following steps to prepare:

[0026] Add 9-carboxyacridine 1.16kg (5.20mol) in the reactor with thermometer and reflux device, cuprous iodide 0.001kg (0.005mol), o-phenanthroline 0.001kg (0.005mol), NMP 2.56kg ( 25.86mol), reacted at 170°C for 6h, evaporated the NMP solvent after the reaction, added 0.56L of water and mixed evenly, filtered to obtain a black crude product, and recrystallized the black crude product with cyclohexane to obtain 0.086kg of acridine as a light yellow solid , with a purity of 99.5% and a yield of 91.7%. The NMR characterization data of the product are consistent with Example 1.

[0027] The preparation method embodiment 3 of acridine of the present invention, synthetic route is as follows:

[0028]

[0029] Specifically adopt the following steps to prepare:

[0030] Add 1.25kg (5.60mol) of...

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Abstract

The invention relates to a preparing method of acridine. The method includes the following step of evenly mixing 9-carboxyl acridine, a catalyst and ligand in an organic solvent for the reaction for 1-8 hours at 140-200 DEG C to obtain the acridine, wherein the ligand is at least one of N,N'-dimethylpiperazine, triethylamine, phenanthroline, substituted phenanthroline, N,N,N',N'-tetramethylethylenediamine, N,N'-dimethylaniline and N,N-diisopropylethylamine. According to the preparing method of the acridine, the acridine is synthesized through one step with 9-carboxyl acridine as the raw material, the reaction is carried out with the presence of the catalyst and the ligand, the reaction process is mild and easy to control, the product is high in purity and yield, the industrial manufacturing cost of the acridine is remarkably reduced, and the good industrial application value is realized.

Description

technical field [0001] The invention belongs to the field of acridine synthesis, in particular to a method for preparing acridine. Background technique [0002] Acridine is an important intermediate of thermally active delayed fluorescent materials, and has important applications in organic electroluminescent diodes. Since the acridine ring has a large conjugation plane, it has a strong π-π interaction in the solid state and has better fluorescence properties, and can be directly used as a luminescent material. In analytical chemistry, according to the fluorescence properties of its metal complexes, it can be used to detect metal ions, and can also be used to synthesize metal complexes with excellent properties for organic light-emitting devices. At the same time, acridine is also an important parent compound for making acridine dyes and drugs (such as acriflavine and quinacrine), and is also used as a fluorescent pH indicator. [0003] At present, the synthesis of acridin...

Claims

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Application Information

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IPC IPC(8): C07D219/02
CPCC07D219/02
Inventor 杨勇胡孝伦马佰位申丽坤李鹏翔韩学哲
Owner ZHENGZHOU SIGMA CHEM
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