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Method for preparing alkylaryl amine compound through microwave synthesis

A technology of alkylaryl and microwave synthesis, which is applied in the chemical industry, can solve the problems of harsh reaction conditions and high environmental costs, and achieve the effects of short reaction time, convenient post-processing, and easy operation

Inactive Publication Date: 2015-02-25
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the above two reactions, aryl halides are used as starting substrates and heavy metals as catalysts, the reaction conditions are harsh and the environmental cost is high

Method used

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  • Method for preparing alkylaryl amine compound through microwave synthesis
  • Method for preparing alkylaryl amine compound through microwave synthesis
  • Method for preparing alkylaryl amine compound through microwave synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of 3-benzylamino-4-hydroxybenzoic acid methyl ester comprises the following steps:

[0023] Add methyl 3-dehydroshikimate (0.37g, 2.0mmol), benzylamine (0.19g, 1.8mmol), p-toluenesulfonic acid (18mg, 0.1mmol), and 5ml dimethyl sulfoxide into the microwave reaction flask at one time middle. The reaction system was reacted at 130° C. for 10 min in a microwave reactor. The reaction was monitored by TLC. After the reaction was completed, after cooling, the reaction solution was poured into 80ml of saturated saline solution, stirred continuously, and a solid was precipitated, filtered by suction, and the solid was recrystallized with dichloromethane-petroleum ether to obtain white crystals of 3-benzylamino-4- Methyl hydroxybenzoate 0.38g, yield: 82%.

[0024] The characterization data of the product is: m.p.147-149°C; 1 H NMR (400MHz, DMSO-d 6 )δ:ppm10.30(s,1H),7.28-7.34(m,4H),7.18-7.22(m,1H),7.10-7.13(dd,J 1 =8.00Hz,J 2 =2.00Hz,1H),6.93(d,J=1.60Hz,1H),...

Embodiment 2

[0027] The preparation of 3-cyclohexylamino-4-hydroxybenzoic acid methyl ester comprises the following steps:

[0028] Methyl 3-dehydroshikimate (0.37g, 2.0mmol), cyclohexylamine (0.22g, 2.2mmol), p-toluenesulfonic acid (36mg, 0.2mmol), 5ml N,N-dimethylformamide once added to a microwave reaction vial. The reaction system was reacted at 120° C. for 15 min in a microwave reactor. The reaction was monitored by TLC. After the reaction was completed, after cooling, the reaction solution was poured into 30ml saturated brine, extracted with ethyl acetate (3×30ml), the extract was washed with water, dried, and the solvent was removed by rotary evaporation. Hexylamino-4-hydroxybenzoic acid methyl ester 0.35g, yield: 70%.

[0029] The characterization data of the product is: m.p.152-154°C; 1 H NMR (400MHz, DMSO-d 6 )δ:ppm10.25(s,1H),7.11(dd,J 1 =8.00Hz,J 2 =2.00Hz,1H),7.03(d,J=2.00Hz,1H),6.72(d,J=8.00Hz,1H),4.39(s,1H),3.74(s,3H),3.21(m,1H ),1.90-1.93(m,2H),1.67-1.70(m,2H),1.57-1...

Embodiment 3

[0032] The preparation of 3-butylamino-4-hydroxybenzoic acid methyl ester comprises the following steps:

[0033] Methyl 3-dehydroshikimate (0.37g, 2.0mmol), n-butylamine (0.15g, 2.0mmol), p-toluenesulfonic acid (3.6mg, 0.02mmol), 5ml N,N-dimethylmethylamine Add to the microwave reaction vial at one time. The reaction system was reacted at 160° C. for 8 min in a microwave reactor. The reaction was monitored by TLC. After the reaction was completed, after cooling, the reaction solution was poured into 30ml of saturated brine, extracted with ethyl acetate (3×30ml), the extract was washed with water, dried, and the solvent was removed by rotary evaporation. Column chromatography gave white crystals of 3-butyl Amino-4-hydroxybenzoic acid methyl ester 0.30g, yield: 68%.

[0034] The characterization data of the product is: m.p.107-109°C; 1 H NMR (400MHz, DMSO-d 6 )δ:ppm10.25(s,1H),7.12(dd,J 1 =8.00Hz,J 2 =2.00Hz,1H),7.00(d,J=2.00Hz,1H),6.72(d,J=8.00Hz,1H),4.74(s,1H),3.74(s,3H...

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Abstract

The invention discloses a method for preparing an alkylaryl amine compound through microwave synthesis. The method comprises the following steps of: reacting 3-dehydrogenated methyl shikimate and an alkylamine compound (formula 3) under the conditions of an organic solvent 1, a catalyst and a microwave, so that the hexatomic ring skeleton of 3-dehydrogenated methyl shikimate is subjected to aromatization; after reaction liquid is cooled, pouring the reaction liquid into a large quantity of saturated salt solutions, fast stirring to precipitate a solid or extracting by using an organic solvent, drying, and carrying out column chromatography to obtain a 3-alkanamine-4-methyl hydroxybenzoate compound (formula I). The method disclosed by the invention can be used for obtaining the 3-alkanamine-4-methyl hydroxybenzoate compound by realizing the amine accelerating aromatization reaction of 3-dehydrogenated methyl shikimate by adopting microwave synthesis, and has the advantages of short reaction time, simplicity and convenience for operation, convenience for post-processing and cleanness in reaction.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a method for synthesizing 3-alkylamino-4-hydroxybenzoic acid methyl ester compounds by microwave. Background technique [0002] Alkylarylamines are an important class of organic compounds, and related structures are widely found in pharmaceutical products. For example: Primaquine (Primaquine) is an 8-aminoquinoline derivative, which can kill the gametocytes of various types of Plasmodium in human blood. It can be used in combination with blood schizonticides to cure benign malaria and reduce drug resistance. occurrence (Journal of Practical Medicine, 2006, 22(19), 2299-2300); melphalan (melphalan) is an amino acid nitrogen mustard, which has a good curative effect on the treatment of ovarian cancer, breast cancer, lymphosarcoma and other malignant tumors. The structures of the above drugs all have structural units of alkylarylamines. [0003] [0004] At present,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/06C07C229/64
Inventor 张恩生邹永徐田龙王德建魏文陈爱民
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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