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Method for preparing N-(5-methyl furfuryl) p-methoxyaniline by using one-pot method

A technology for p-methoxyaniline and methyl furfuryl, which is applied in the field of compound synthesis, can solve the problems of high preparation cost of methoxyaniline, cumbersome process, low yield and the like, achieves maximum utilization of resources and simplifies operation process , the effect of reducing production costs

Inactive Publication Date: 2018-03-06
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve the problems of high preparation cost, cumbersome process and low yield of N-(5-methylfurfuryl)-p-methoxyaniline, the present invention provides a simple one-pot method for adding heterogeneous catalyst under hydrogen atmosphere. Method, a method for preparing N-(5-methylfurfuryl) p-methoxyaniline by direct reductive amination of 5-methylfurfural and p-methoxyaniline

Method used

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  • Method for preparing N-(5-methyl furfuryl) p-methoxyaniline by using one-pot method

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Embodiment 1

[0022] In the autoclave with a magnetic stirring bar, add 10mg Pd / C, 500ul 5-methylfurfural, 20ml ethyl acetate, 0.6783g p-methoxyaniline successively, close the autoclave, and replace the air in the reactor with hydrogen , and ensured that the initial hydrogen pressure of the reaction was 1.2Mpa, the high-pressure reactor was placed in an electric heating mantle, the temperature was raised to 90°C, and the reaction was stirred for 4h. Gas chromatographic analysis was carried out after the reaction, and it was calculated by the area normalization method that the conversion rates of the substrate 5-methylfurfural and p-methoxyaniline reached 96.87% and 88.60% respectively, and the intermediate product N-(5-methoxyaniline in the system The percentages of N-(5-methylfurfuryl)-p-methoxyphenylimine and the target product N-(5-methylfurfuryl)-p-methoxyaniline were 31.04% and 55.10%, respectively.

[0023] figure 1 It is the gas chromatogram of the reaction liquid obtained in the pr...

Embodiment 2

[0027] In the autoclave with a magnetic stirring bar, add 15mg Pd / C, 500ul 5-methylfurfural, 20ml ethyl acetate, 0.6781g p-methoxyaniline successively, close the autoclave, and replace the air in the reactor with hydrogen , and ensured that the initial hydrogen pressure of the reaction was 0.8Mpa, the high-pressure reactor was placed in an electric heating mantle, the temperature was raised to 70°C, and the reaction was stirred for 2h. Gas chromatographic analysis was carried out after the reaction, and calculated by the area normalization method, the conversion rates of the substrate 5-methylfurfural and p-methoxyaniline reached 94.30% and 87.22% respectively, and the intermediate product N-(5-methoxyaniline in the system The percentages of N-(5-methylfurfuryl)-p-methoxyphenylimine and the target product N-(5-methylfurfuryl)-p-methoxyaniline were 26.70% and 97.10%, respectively.

Embodiment 3

[0029] In the autoclave with magnetic stirring bar, add 10mg Pd / C, 500ul 5-methylfurfural, 20ml ethanol, 0.6779g p-methoxyaniline successively, close the autoclave, and replace the air in the reactor with hydrogen, and Ensure that the initial hydrogen pressure of the reaction is 1.2Mpa, place the high-pressure reactor in an electric heating mantle, raise the temperature to 90°C, and stir for 4 hours. Gas chromatographic analysis was carried out after the reaction, and the calculation by area normalization method showed that the conversion rates of substrate 5-methylfurfural and p-methoxyaniline reached 100% and 91.60% respectively, and the intermediate product N-(5-methoxyaniline in the system The percentages of N-(5-methylfurfuryl)-p-methoxyphenylimine and the target product N-(5-methylfurfuryl)-p-methoxyaniline were 25.44% and 66.15%, respectively.

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Abstract

The invention discloses a method for preparing N-(5-methyl furfuryl) p-methoxyaniline by using a one-pot method. The method comprises the following steps: sequentially putting a multi-phase hydrogenation catalyst, 5-methyl furfural, a solvent and p-methoxyaniline into a reaction container, stirring in a hydrogen atmosphere under normal pressure to 2.0MPa at normal temperature to 100 DEG C, performing a reaction for 0.2-30 hours, and separating the catalyst from a product. By adopting the method, operation procedures are simplified, material loss caused by middle steps is avoided, and the maximum resource utilization is achieved; under appropriate process conditions, the reaction time is greatly shortened, the production cost is reduced, and the production efficiency is improved; and the method is implemented under gentle conditions, production equipment is not highly required, and principles of safe production are met.

Description

technical field [0001] The present invention belongs to the field of compound synthesis methods. Background technique [0002] N-(5-methylfurfuryl)-p-methoxyaniline (CAS 95124-39-3; C 13 h 15 NO 2 ; 2-Furanmethanamine, N-(4-methoxyphenyl)-5-methyl-) has certain antibacterial function (Fedor I. Zubkov, Vladimir P.Zaytsev, Eugeniya V. Nikitina, et al. Tetrahedron, 2011, 9148-9163 ), usually prepared by a two-step method, that is, first reacting 5-methylfurfural with p-methoxyaniline to obtain N-(5-methylfurfuryl)-p-methoxyphenylimine containing a carbon-nitrogen double bond, Then the target product N-(5-methylfurfuryl) p-methoxyaniline is obtained by reducing C=N with a hydrogenation reagent, wherein the hydrogenation reagent includes a magnesium / methanol reduction system, sodium borohydride, etc. (Zivko Klepo, Kresimir Jakopcic.J. Chem. Eng. Data, 1985, 235-237; Fernando D. Suvire, Maximiliano Sortino, Vladimir V. Kouznetsov, et al. Enriz. Bioorgan. Med. Chem., 2006, 1851...

Claims

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Application Information

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IPC IPC(8): C07D307/52
Inventor 肖建军邱祖民杨维冉姜俊彭阳
Owner NANCHANG UNIV
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