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O-phenylenediamine schiff base derivative as well as preparation method and application thereof

A technology of o-phenylenediamine and nitro-o-phenylenediamine, applied in the field of preparation of o-phenylenediamine Schiff base derivatives and o-phenylenediamine Schiff base derivatives, can solve difficult separation and purification, long reaction time , many side reactions and other problems, to achieve the effect of good chemical stability, short reaction time, easy operation and control

Active Publication Date: 2017-03-15
重庆信人科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the traditional preparation method of Schiff base is generally obtained by condensation reaction of a compound containing an active carbonyl group with an amine in an organic solvent, which requires the use of an organic solvent and a catalyst, and the reaction time is long, and there are many side reactions, making it difficult to separate and purify , has the disadvantages of high energy consumption and large pollution

Method used

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  • O-phenylenediamine schiff base derivative as well as preparation method and application thereof
  • O-phenylenediamine schiff base derivative as well as preparation method and application thereof
  • O-phenylenediamine schiff base derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a 25ml hydrothermal reaction kettle, add 10ml of water (that is, the filling degree is 40%), and 3mmol of 4-nitro-o-phenylenediamine and 3mmol of benzaldehyde, and react at 120° C. for 20 minutes. After the reaction is completed, the reaction kettle is cooled to room temperature, and the reaction product is filtered, dried, recrystallized and dried to obtain the target product.

[0029] figure 1 is the o-phenylenediamine Schiff base derivative obtained in Example 1 of the present invention 1 H-NMR spectrum.

[0030] 1 H-NMR (400MHz, DMSO-d 6 )δ: 8.85(s,1H), indicating that the Schiff base has been successfully prepared, 8.03-8.10(m,2H), 8.02(m,1H), 7.89(m,1H), 7.49-7.58(m,3H), 6.79 (m, 1H), 6.76 (m, 2H).

[0031] figure 2 It is the o-phenylenediamine Schiff base derivative obtained in Example 1 of the present invention (concentration is 1×10 -5 mol / L) in cyclohexane, dichloromethane, normalized fluorescence emission spectrum in absolute ethanol (excitation wa...

Embodiment 2

[0033] In a 25ml hydrothermal reaction kettle, add 10ml of water (that is, the filling degree is 40%), and 2mmol of 4-nitro-o-phenylenediamine and 2mmol of benzaldehyde, and react at 120° C. for 40 minutes. After the reaction is finished, the reactor is cooled to room temperature, and the reaction product is filtered, dried, recrystallized and dried to obtain the target product.

[0034] image 3 is the o-phenylenediamine Schiff base derivative obtained in Example 2 of the present invention 1 H-NMR spectrum.

[0035] 1 H-NMR (400MHz, DMSO-d 6 )δ: 8.82(s,1H), indicating that the Schiff base has been successfully prepared, 8.10(m,2H), 8.02(m,1H), 7.92(m,1H), 7.52(m,3H), 6.81(m, 1H), 6.73-6.79 (m, 2H).

Embodiment 3

[0037] In a 50ml hydrothermal reaction kettle, add 10ml of water (ie, the filling degree is 20%), and 3mmol of 4-nitro-o-phenylenediamine and 3mmol of benzaldehyde, and react at 100°C for 90 minutes. After the reaction is finished, the reactor is cooled to room temperature, and the reaction product is filtered, dried, recrystallized and dried to obtain the target product.

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Abstract

The invention discloses an o-phenylenediamine schiff base derivative as well as a preparation method and application thereof. The structural formula of the derivative is as shown in the specification. During preparation, firstly, a certain volume of water and an appropriate amount of 4-nitryl o-phenylenediamine and benzaldehyde are added into a hydrothermal reaction kettle, and then a reaction is carried out at the temperature of 100 to 150 DEG C for 10 to 90 minutes; and after the reaction is finished, the reaction kettle is cooled to room temperature, and then reaction products are filtered, dried, recrystallized and dried, so that the o-phenylenediamine schiff base derivative can be obtained. The preparation method is non-poisonous or harmless, does not use any catalyst, and mainly utilizes high diffusion coefficient and high solubility of high-temperature water, so that the reaction is carried out efficiently and conveniently. The o-phenylenediamine schiff base derivative disclosed by the invention is high in chemical stability and high in solubility, and has a luminescent property.

Description

technical field [0001] The invention relates to a Schiff base, in particular to an o-phenylenediamine Schiff base derivative, and also relates to a preparation method and application of an o-phenylenediamine Schiff base derivative. Background technique [0002] Schiff base mainly refers to a class of organic compounds containing imine or imine groups (carbon-nitrogen double bond, -RC=N-), usually formed by condensation of compounds containing active carbonyl groups and primary amines. Schiff bases and their complexes have excellent biological activities such as antibacterial, anticancer, antiviral, and herbicidal, as well as special optical and electromagnetic properties. Therefore, it has aroused extensive research interests of researchers in the fields of medicine, biology, catalysis, and functional materials in recent years. [0003] However, the traditional preparation method of Schiff base is generally obtained by condensation reaction of a compound containing an activ...

Claims

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Application Information

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IPC IPC(8): C07C251/24C07C249/02C09K11/06
CPCC07C249/02C07C251/24C09K11/06C09K2211/1007
Inventor 黄杰彭锋
Owner 重庆信人科技发展有限公司
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