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Method for preparing N, 2-allyl anilines

A technology for allylaniline and diallylaniline, which is applied in the field of preparation of N,2-allylaniline compounds, and can solve the problem that the single and double substitution products are difficult to control, the single and double substitutions are difficult to control, and the reaction time is long. problem, to achieve the effect of low production cost, short reaction time and simple post-processing

Inactive Publication Date: 2012-07-25
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the method for synthesizing N,2-allyl aniline compounds is generally through the reaction of allyl alcohol and aniline under the condition of palladium as a catalyst. There are disadvantages such as long reaction time, expensive catalyst, and difficult control of single and double substitution in the product.
Lothar W. Bieber et al. prepared N,2-allylaniline by reacting propene bromide and nitrobenzene. This reaction also has the disadvantages of long reaction time and difficult control of single and double substitution products.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Synthesis of N,N-diallylaniline compound: Dissolve aniline (0.93 g, 10.00mmol) in chloroform (10.00ml), add triethylamine (4.05g, 40.00mmol), at 65 Slowly add bromopropene (4.84g, 40.00mmol) dropwise at ℃. The whole reaction process is tracked by thin-layer chromatography (TCL), that is, samples are taken every 10 minutes, and the reaction solution is dripped on the silica gel plate with a capillary tube. Sample and raw material liquid aniline spotting, the two spots are on the same straight line, and then put the silica gel plate into the exhibition bottle containing the mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:100. 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 aniline of the raw material liquid in the reaction solution, it indicates that the reaction is complete. The reaction time is 4 h, and the reaction solution ...

Embodiment 2

[0030] (1) Synthesis of N,N-diallylaniline compound: Dissolve aniline (0.93 g, 10.00mmol) in chloroform (10.00ml), add triethylamine (3.04g, 30.00mmol), at 40 Propyl bromide (3.63g, 30.00mmol) was slowly added dropwise at ℃, and the whole reaction process was tracked by thin-layer chromatography (TCL). The reaction time was 6 h, and the reaction solution was obtained; The crude product N,N-diallylaniline compound is obtained by extraction, and the pure product N,N-diallylaniline compound is obtained after column separation. The yield was 75%.

[0031] The structure and characterization of the product are the same as in Example 1.

[0032] (2) Preparation of N,2-allylaniline compound: Add N,N-diallylaniline compound (0.14g, 8.00mmol) and anhydrous aluminum chloride (0.053g, 0.40mmol) to the reaction In the flask, add chlorobenzene as a solvent, and stir at 160°C for 2 hours; after the reaction is complete (TLC detection), evaporate chlorobenzene, add ethyl acetate, wash with ...

Embodiment 3

[0035](1) Synthesis of N,N-diallylaniline compound: Dissolve aniline (0.93 g, 10.00mmol) in chloroform (10.00ml), add triethylamine (5.06g, 50.00mmol), and dissolve at 70 Slowly add bromopropene (6.05g, 50.00mmol) dropwise at ℃, the whole reaction process was tracked by thin-layer chromatography (TCL), and the reaction time was 2 h to obtain the reaction solution; The crude product N,N-diallylaniline compound is obtained by extraction, and the pure product N,N-diallylaniline compound is obtained after column separation. The yield was 80%.

[0036] The structure and characterization of the product are the same as in Example 1.

[0037] (2) Preparation of N,2-allylaniline compound: Add N,N-diallylaniline compound (0.14g, 8.00mmol) and anhydrous aluminum chloride (0.20g, 1.50mmol) to the reaction In the flask, add chlorobenzene as a solvent, and stir at 120°C for 6 hours; after the reaction is complete (TLC detection), evaporate chlorobenzene, add ethyl acetate, wash with water...

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PUM

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Abstract

The invention discloses a method for preparing N, 2-allyl anilines, which belongs to the technical field of chemical synthesis. The method includes: using chloroform as solvent and using triethylamine as acid-binding agent to lead aromatic amine to be in reaction with bromopropylene, extracting, and column chromatographic separating to obtain N, N-diallyl anilines; and using chlorobenzene as solvent, allowing the N, N-diallyl anilines to be in reaction with anhydrous aluminium chloride, extracting, and column chromatographic separating to obtain N, 2-allyl anilines. Usage of noble metal catalysts is avoided, so that cost is reduced and the method is favorable for environment. Further, the method is simple in process procedure, mild in reaction conditions, short in reaction time, simple in post-treatment and simple and safe in operation, and has bright industrial application prospect.

Description

Technical field [0001] The present invention is an organic synthetic chemistry field, involving a preparation method for N, 2-alpha-acrobine-based compounds. Background technique [0002] N-replaced 1-benzene and nitrogen miscellaneous substance is an important type of heterocyclic intermediate. Many 1-benzene and nitrogen miscellaneous substances show strong biological activity. This type of substance is derivative.For example, OPC-31260 (formerly flower greenin) and dehumin tablets have a certain effect on the treatment of heart disease.N, 2-allybiniline is a key intermediate of synthetic 1-benzene and nitrogen miscellaneous substance. The structure is as follows: [0003] [0004] At present, the method of synthetic N, 2-hydraxililine compounds is generally reacted under the conditions of catalysts and aniline as a catalyst. Such methods have long reactions, expensive catalysts, and single and double replacement in products in products.Not easy to control the disadvantages.L...

Claims

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Application Information

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IPC IPC(8): C07C211/48C07C209/68
Inventor 杨文龙张鹏云姬鹏燕刘茵姚桃花
Owner NORTHWEST NORMAL UNIVERSITY
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