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Preparation method of diindolylmethane derivative through catalysis

A technology for the catalytic preparation of diindolylmethane, which is applied in the field of catalytic preparation of diindolylmethane derivatives, can solve the problems of high cost and complex preparation of acidic ionic liquids, and achieve environmental pollution reduction, high yield, and good catalytic activity Effect

Inactive Publication Date: 2013-10-09
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation of the acidic ionic liquid is relatively complicated and expensive (An efficient one-pot synthesis of bis(indolyl)methanes catalyzed by ionic liquid with multi-SO 3 H groups under ambient temperature in water, World Applied Science Journal, 2011,15(6):877-884)

Method used

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  • Preparation method of diindolylmethane derivative through catalysis
  • Preparation method of diindolylmethane derivative through catalysis
  • Preparation method of diindolylmethane derivative through catalysis

Examples

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Effect test

Embodiment 1

[0019] Example 1: Add 2 mmol of indole, 1 mmol of benzaldehyde, 0.01 mmol of catalyst and 2 mL of water into a 25 mL single-neck flask with a stir bar. The reaction was stirred vigorously at 25°C, and thin-layer chromatography (TLC) (developing solvent: n-hexane: ethyl acetate=4:1) followed the progress of the reaction. When the reaction is applied for 6 minutes, the reaction pressure is one atmosphere. After the completion of the reaction, suction filtration, the obtained filter residue was recrystallized with 98% ethanol aqueous solution and dried to obtain pure diindophenylmethane with a yield of 93%. The filtrate (including catalyst and unreacted raw materials) is directly used in the next reaction without any treatment.

Embodiment 2

[0020] Example 2: Add 2 mmol of indole, 1 mmol of p-chlorobenzaldehyde, 0.01 mmol of catalyst, and 2 mL of water into a 25 mL single-necked flask with a stir bar. The reaction was stirred vigorously at 25°C, and thin-layer chromatography (TLC) (developing solvent: n-hexane: ethyl acetate=4:1) followed the progress of the reaction. When the reaction is applied for 8 minutes, the reaction pressure is one atmosphere. After the reaction, the filter residue was recrystallized with a 98% ethanol aqueous solution and dried to obtain pure p-chlorophenyl diindolylmethane with a yield of 94%. The filtrate (including catalyst and unreacted raw materials) is directly used in the next reaction without any treatment.

Embodiment 3

[0021] Example 3: Add 2 mmol of indole, 1 mmol of p-nitrobenzaldehyde, 0.01 mmol of catalyst and 4 mL of water into a 25 mL single-neck flask with a stir bar. The reaction was stirred vigorously at 27° C., and thin-layer chromatography (TLC) (developing solvent: n-hexane: ethyl acetate=4:1) followed the progress of the reaction. When the reaction is applied for 3 minutes, the reaction pressure is one atmosphere. After the completion of the reaction, suction filtration, the obtained filter residue was recrystallized with 98% ethanol aqueous solution and dried to obtain pure p-nitrophenyl diindolylmethane with a yield of 97%. The filtrate (including catalyst and unreacted raw materials) is directly used in the next reaction without any treatment.

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Abstract

The invention provides a preparation method of diindolylmethane derivative through catalysis, belonging to the technical field of organic chemistry synthesis. During a reaction of preparing the diindolylmethane derivative, a mole ratio of indole and aromatic aldehyde is 2-5 : 1, a molar amount of a catalyst is 1-3 % of the amount of aromatic aldehyde, a volume amount (mL) of a reaction solvent water is 2-10 times of a molar amount (mmol) of the aromatic aldehyde, a reaction temperature is 25-30 DEG C, a reaction time is 2-30 minutes, and a reaction pressure is an atmospheric pressure. After the reaction, the product is filtered through pumping, and filter residues are recrystallized by 98 % aqueous ethanol and then dried to obtain the pure diindolylmethane derivative. The catalyst contained in the filtrate can be recycled without any treatment. Compared with preparation methods using traditional proton acid and Lewis acid as catalysts, the method provided by the invention is little in reaction time, mild in reaction conditions and few in catalyst amount, and the catalyst can be recycled.

Description

Technical field [0001] The invention belongs to the technical field of organic chemistry synthesis, and specifically relates to a method for catalytically preparing diindolylmethane derivatives. Background technique [0002] Diindolylmethane derivatives are very important among many indole derivatives. They are widely present in natural products and have many pharmacological and physiological activities. For example, it can promote the metabolism of estrogen in the human body, can regulate the hormone metabolites secreted by certain cancer cells, and is an effective anti-cancer drug. Therefore, the synthesis of diindolylmethane derivatives has attracted widespread attention. At present, most of the preparations of these compounds are mainly carried out in traditional organic solvents, usually using expensive or toxic Lewis acids as catalysts. At the same time, there are disadvantages such as long reaction time, low yield and serious environmental pollution. Therefore, the devel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C07D209/10C07D209/18
CPCY02P20/584
Inventor 岳彩波吴胜华储昭莲
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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