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Preparation method for imido naphthol compound

An imino-naphthol and compound technology, which is applied in the field of preparation of imino-naphthol compounds, can solve the problems of harsh reaction conditions and difficult preparation of raw materials, and achieves short reaction time, good industrial application prospect and mild reaction conditions. Effect

Active Publication Date: 2014-12-17
盐城盐西幸福产业发展有限公司
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Problems solved by technology

[0003]In 1991, Katritzky et al. reacted benzotriazol-based naphthol compounds with n-butyllithium or Grignard reagents at -78°C, which can be directly Generate iminonaphthol compounds, but the reaction conditions are harsh and the raw materials are not easy to prepare (Chemische Berichte, 1991, 124, 1431)
In 2003, Saidi et al. used diethyl ether as a solvent, lithium perchlorate and trimethylchlorosilane as a catalyst to react β-naphthol, aromatic aldehydes and aromatic amines at room temperature to generate saturated aminonaphthols. Although the reaction time is only 15 minutes, the highest yield is only 78% (Tetrahedron: Asymmetry (Tetrahedron: Asymmetry), 2003, 14, 398)
According to the reports of the known literature, the three-component reaction of β-naphthol, aromatic aldehydes and aromatic amines all generates saturated aminonaphthols, and the three react to generate unsaturated aminonaphthols not yet reported

Method used

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  • Preparation method for imido naphthol compound
  • Preparation method for imido naphthol compound
  • Preparation method for imido naphthol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 A preparation method of iminonaphthol compounds, the method refers to: catalyst aluminum powder, aromatic aldehyde compound benzaldehyde, aromatic amine compound aniline and β-naphthol are added to water in sequence, and the temperature is 50 ℃ The reaction was carried out under certain conditions, and the whole reaction process was tracked by thin layer chromatography, that is, samples were taken every 5 minutes, and the reaction solution was dripped on the silica gel plate with a capillary tube, and the raw material solution β-naphthol, aniline and benzaldehyde were spotted. , the four spots are on the same straight line, and then put the silica gel plate into the exhibition bottle filled with a mixture of petroleum ether and ethyl acetate with a volume ratio (mL / mL) of 30:1. After the plate movement is completed, put the silica gel plate under an ultraviolet lamp or an iodine bottle for observation. If there is no point flush with the raw material soluti...

Embodiment 2

[0022] Example 2 A kind of preparation method of iminonaphthol compound, this method refers to: add catalyst cobalt powder, aromatic aldehyde compound benzaldehyde, aromatic amine compound 2-methylaniline and β-naphthol into water successively, at temperature The reaction was carried out under the condition of 70°C, and the whole reaction process was carried out according to Example 1 Described thin-layer chromatography tracking, obtains reaction solution; This reaction solution presses Example 1 Described method obtains the iminonaphthol compound of product I after extracting, drying, concentrating, and column chromatography separation successively, and the product structural formula is as follows (Ar in the structural formula 1 = phenyl, Ar 2 =2-methylphenyl):

[0023]

[0024] Among them: the molar ratio of cobalt powder to β-naphthol is 1:18, the molar ratio of β-naphthol to benzaldehyde is 1:1, the molar ratio of β-naphthol to 2-methylaniline is 1:1.3, The mo...

Embodiment 3

[0026] Example 3 A kind of preparation method of iminonaphthol compound, this method refers to: adding catalyst zinc powder, aromatic aldehyde compound benzaldehyde, aromatic amine compound 4-methylaniline and β-naphthol into water successively, at temperature The reaction was carried out under the condition of 60°C, and the whole reaction process was carried out according to Example 1 Described thin-layer chromatography tracking, obtains reaction solution; This reaction solution presses Example 1 Described method obtains the iminonaphthol compound of product I after extracting, drying, concentrating, and column chromatography separation successively, and the product structural formula is as follows (Ar in the structural formula 1 = phenyl, Ar 2 =4-methylphenyl):

[0027]

[0028] Among them: the molar ratio of zinc powder to β-naphthol is 1:10, the molar ratio of β-naphthol to benzaldehyde is 1:1, the molar ratio of β-naphthol to 4-methylaniline is 1:1, The molar...

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Abstract

The invention relates to a method for preparing iminonaphthol compounds. The method refers to adding catalysts, aromatic aldehyde compounds, aromatic amine compounds and naphthol into water in sequence, and proceeding at a temperature of 20 to 80°C. Reaction, after the reaction is complete, the reaction solution is obtained; the reaction solution is extracted, dried, concentrated, and separated by column chromatography in sequence according to the conventional method to obtain the product I or product II, and the product structural formula is as follows: The invention has mild conditions, short reaction time, simple operation, high yield, environmental protection, large-scale production can be realized, and good industrial application prospect.

Description

technical field [0001] The invention relates to the field of organic synthetic chemistry, in particular to a preparation method of iminonaphthol compounds. Background technique [0002] Imino naphthols are an important class of intermediates in organic synthesis and pharmaceutical synthesis, which can be used to construct synthetic fragments of anticancer drugs, antibacterial drugs and anti-HIV virus drug molecules. On the other hand, symmetrical iminonaphthols have a certain degree of fluorescence, can respond to changes in the pH value of the solution, and can selectively recognize some anions, so they are widely used in the design and manufacture of fluorescent chemical sensors. widespread attention of the people. [0003] In 1991, Katritzky et al. reacted benzotriazol-based naphthols with n-butyllithium or Grignard reagents at -78°C to directly generate imino-naphthols, but the reaction conditions were harsh. The starting materials are also not easy to prepare (Chemisc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/24C07C249/02C07C255/61C07C253/30
Inventor 杜正银刘伟黄莉娜
Owner 盐城盐西幸福产业发展有限公司
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