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Method for catalyzing the carbon-hydrogen bond alkylation reaction of aromatic amines

A carbon-hydrogen bond alkyl and aromatic amine technology, which is applied in the field of catalyzing the carbon-hydrogen bond alkylation reaction of aromatic amines, can solve problems such as hindering the alkylation of aromatic amines, and achieves improved reaction efficiency, mild reaction conditions, and reaction operation. easy effect

Active Publication Date: 2020-04-10
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of reaction usually requires a Lewis acid as a catalyst, and the coordination between the amine substrate and the Lewis acid hinders the alkylation of the aromatic amine, making the amine substrate generally unsuitable for the classic acid-catalyzed reaction system.

Method used

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  • Method for catalyzing the carbon-hydrogen bond alkylation reaction of aromatic amines
  • Method for catalyzing the carbon-hydrogen bond alkylation reaction of aromatic amines
  • Method for catalyzing the carbon-hydrogen bond alkylation reaction of aromatic amines

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Experimental program
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Effect test

Embodiment 1

[0031] The present embodiment provides a kind of utilizing 10mol% [Ph 3 C][B(C 6 f 5 ) 4 ] Catalyzing the method for the alkylation reaction of styrene and 1,2,3,4-tetrahydroquinoline under the condition of 60 DEG C, the specific steps are as follows:

[0032] 46mg (0.05mmol) of [Ph 3 C][B(C 6 f 5 ) 4 ] was dissolved in 2 mL of chlorobenzene, 0.11 mL (1.0 mmol) of styrene and 0.063 mL (0.5 mmol) of 1,2,3,4-tetrahydroquinoline were added to the solution, the tube was sealed, and the Under the condition of argon protection, the reaction was carried out at 60° C. for 12 h. After the reaction, 111 mg of the target product was obtained by column chromatography (ethyl acetate / petroleum ether=1 / 100), with a yield of 94%. The structural formula of target product is as follows:

[0033]

Embodiment 2

[0035] The present embodiment provides a kind of utilization 5mol% [Ph 3 C][B(C 6 f 5 ) 4 ] Catalyzing the method for the alkylation reaction of styrene and 1,2,3,4-tetrahydroquinoline under the condition of 60 DEG C, the specific steps are as follows:

[0036] 23mg (0.025mmol) of [Ph 3 C][B(C 6 f 5 ) 4 ] was dissolved in 2 mL of chlorobenzene, 0.11 mL (1.0 mmol) of styrene and 0.063 mL (0.5 mmol) of 1,2,3,4-tetrahydroquinoline were added to the solution, the tube was sealed, and the Under the condition of argon protection, the reaction was carried out at 60° C. for 12 h. After the reaction was completed, 89 mg of the target product was obtained by column chromatography (ethyl acetate / petroleum ether=1 / 100), with a yield of 75%. The structural formula of target product is as follows:

[0037]

[0038] In the above reaction, styrene, 1,2,3,4-tetrahydroquinoline and [Ph 3 C][B(C 6 f 5 ) 4 ] The mol ratio, reaction temperature and time can also be changed accordin...

Embodiment 3

[0043] The present embodiment provides a kind of utilizing 10mol% [Ph 3 C][B(C 6 f 5 ) 4 ] Catalyzing the method for the alkylation reaction of styrene and 6-methyl-1,2,3,4-tetrahydroquinoline under the condition of 80 DEG C, the specific steps are as follows:

[0044] 46mg (0.05mmol) of [Ph3 C][B(C 6 f 5 ) 4 ] was dissolved in 2mL of chlorobenzene, 0.11mL (1.0mmol) styrene and 74mg (0.5mmol) 6-methyl-1,2,3,4-tetrahydroquinoline were added to the solution, the tube was sealed, and in anhydrous , Oxygen-free and under the protection of argon, react at 80°C for 12h. After the reaction, 119 mg of the target product was obtained by column chromatography (ethyl acetate / petroleum ether=1 / 100), with a yield of 95%. The structural formula of target product is as follows:

[0045]

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Abstract

The invention relates to a method for catalyzing hydrocarbon bond alkylation reaction of aromatic amine. The method comprises the step of reacting by virtue of olefin represented by a formula (1) and secondary aromatic amine represented by a formula (2) at 25-130 DEG C in an aprotic solvent under the catalysis of triphenyl carbon tetra(pentafluorophenyl)borate, wherein the formula (1) and the formula (2) are as follows: formulae (shown in the description), wherein R1 is selected from C1-C6 alkyl or aryl, R2 is selected from hydrogen, methyl or halogen, and R3 is selected from C1-C4 alkyl or -(CH2)n- (n is equal to 1 and 2). The method has the beneficial effects that the hydrocarbon bond alkylation reaction efficiency of aromatic amine is effectively improved, the raw materials are easily available, the operation is simple and convenient, reaction conditions are relatively mild, the yield is relatively high, and the application range of a substrate is relatively wide.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for catalyzing the carbon-hydrogen bond alkylation reaction of aromatic amines. Background technique [0002] The efficient synthesis of amine compounds is one of the most widely studied topics in the field of organic chemistry in the past century. Amines are an extremely important class of compounds that exist in large quantities in various living organisms and are widely used in fertilizers, pesticides and various fine chemicals. Carrying out relevant research work not only has important theoretical significance, but also has potential application value. [0003] The carbon-hydrogen bond (C-H bond) alkylation reaction of aromatic amine is a reaction to directly modify the C-H bond, which has 100% atom economy and is the most direct and efficient method for preparing aniline derivatives. This type of reaction usually requires a Lewis acid as a catalyst, and the coordi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C07D215/14C07D215/12C07D209/08C07C209/68C07C211/48
CPCC07C209/68C07D209/08C07D215/06C07D215/12C07D215/14C07C211/48
Inventor 袁丹朱文果孙秋
Owner SUZHOU UNIV