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The preparation method of 5-amino-8-hydroxyquinoline

A hydroxyquinoline and amino technology, applied in the field of preparation of amino compounds, can solve the problems of complicated operation, high toxicity of recrystallization solvent benzene, product needs to be recrystallized, etc., and achieves the effects of simple method, saving toxic solvent and low cost

Inactive Publication Date: 2011-12-28
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthetic method of 5-amino-8-hydroxyquinoline has literature report at present, and people such as Wei Changmei once reported the synthetic method of 5-amino-8-hydroxyquinoline in 2004, and this method is complicated to operate, and the product of generation needs recrystallization, The recrystallization solvent benzene used is highly toxic

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation method of 5-amino-8-hydroxyquinoline, comprises the steps:

[0021] (1) 5-nitro-8-hydroxyquinoline is added to solvent isopropanol, adding mass content is the Pd / C catalyst of 5%, is warming up to 70 DEG C; Described mass content is the Pd / C catalyst of 5% and The ratio of 5-nitro-8-hydroxyquinoline is 25g: 1mol;

[0022] (2) join the hydrazine hydrate aqueous solution that mass concentration is 80% in the mixed liquor that step (1) obtains with the time of 30min, the ratio of described hydrazine hydrate and the amount of 5-nitro-8-hydroxyquinoline substance is 1:1.8;

[0023] (3) Reflux at 80-85° C. for 4 h, filter while hot, and let the filtrate stand for 10 h to precipitate brown-yellow columnar crystals of 5-amino-8-hydroxyquinoline with a yield of 58.0%.

Embodiment 2

[0025] The preparation method of 5-amino-8-hydroxyquinoline, comprises the steps:

[0026] (1) 5-nitro-8-hydroxyquinoline is added to solvent isopropanol, adding mass content is the Pd / C catalyst of 5%, is warming up to 70 DEG C; Described mass content is the Pd / C catalyst of 5% and The ratio of 5-nitro-8-hydroxyquinoline is 25g: 1mol;

[0027] (2) join the hydrazine hydrate aqueous solution that mass concentration is 80% in the mixed solution that step (1) obtains with the time of 35min, the ratio of the amount of described hydrazine hydrate and 5-nitro-8-hydroxyquinoline substance is 1:1.5;

[0028] (3) Reflux at 80-85° C. for 3 h, filter while hot, and let the filtrate stand for 10 h to precipitate brown-yellow 5-amino-8-hydroxyquinoline columnar crystals with a yield of 62.8%.

Embodiment 3

[0030] The preparation method of 5-amino-8-hydroxyquinoline, comprises the steps:

[0031] (1) 5-nitro-8-hydroxyquinoline is added to solvent isopropanol, adding mass content is the Pd / C catalyst of 5%, is warming up to 70 DEG C; Described mass content is the Pd / C catalyst of 5% and The ratio of 5-nitro-8-hydroxyquinoline is 25g: 1mol;

[0032] (2) join the hydrazine hydrate aqueous solution that mass concentration is 80% in the mixed solution that step (1) obtains with the time of 25min, the ratio of the amount of described hydrazine hydrate and 5-nitro-8-hydroxyquinoline substance is 1:2.0;

[0033] (3) Reflux at 80-85° C. for 5 h, filter while hot, and let the filtrate stand for 12 h to precipitate brown-yellow columnar crystals of 5-amino-8-hydroxyquinoline with a yield of 70.0%.

[0034] Example 3

[0035] The preparation method of 5-amino-8-hydroxyquinoline, comprises the steps:

[0036] (1) 5-nitro-8-hydroxyquinoline is added to solvent isopropanol, adding mass cont...

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PUM

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Abstract

The invention discloses a preparation method of 5-amino-8-hydroxyquinoline. The steps are: (1) adding 5-nitro-8-hydroxyquinoline into isopropanol as a solvent, adding a Pd / C catalyst, and raising the temperature; (2) ) adding the hydrazine hydrate aqueous solution to the mixed solution obtained in step (1); (3) reflux reaction, filtering while hot, and standing the filtrate for 8-12 hours, and the brown-yellow 5-amino-8-hydroxyquinoline columnar crystals are precipitated. The invention has high reaction yield. The method is simple and convenient, the brownish-yellow 5-amino-8-hydroxyquinoline columnar crystals are obtained through the reaction of the present invention, and the step of recrystallization is not required, thus saving the toxic solvent used in the prior art when the product is recrystallized, and the cost is low. Green.

Description

technical field [0001] The invention relates to a preparation method of amino compounds, in particular to a preparation method of 5-amino-8-hydroxyquinoline. Background technique [0002] 8-Hydroxyquinoline metal complexes are an important organic electroluminescent material. This kind of complexes has the advantages of high fluorescence efficiency, easy purification and stable properties. By studying the luminescent mechanism of this kind of complexes, it is found that different ligands have an important influence on the luminescent properties of the complexes. The modification of the ligand and the introduction of substituents are usually on the phenolic oxygen ring or the pyridine ring, mainly at the C-5 position, and secondly at the C-2 position. Using 5-amino-8-hydroxyquinoline as a raw material, it reacts with a series of aromatic aldehydes to form a Schiff base, thereby forming a larger conjugated system and improving the fluorescence properties of the complex. In a...

Claims

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Application Information

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IPC IPC(8): C07D215/38
Inventor 崔建中胡耀敏高洪苓胡丛丛屈静伊勇玲
Owner TIANJIN UNIV
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