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Method for preparing 9-aryl multi-hydrogen acridine ramification through catalysis
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A technology for catalytic preparation and derivatives, applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problem of large loss, achieve high acid density, good catalytic activity, and high yield Effect
Inactive Publication Date: 2015-01-21
ANHUI UNIVERSITY OF TECHNOLOGY
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[0004] The purpose of the present invention is to overcome the shortcoming that the amount of acidic ionic liquid catalyst that exists in the prior art and the amount of loss in recycling are all very large, and provide a kind of bissulfonate acidic ionic liquid with higher acidity as catalyzer, product purity Catalyzed method for preparing 9-aryl polyhydroacridine derivatives with high yield and high yield
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Embodiment 1
[0019] Add 10mmol benzaldehyde, 20mmol 1,3-cyclohexanedione, 30mmol ammonium acetate, 25mL absolute ethanol and 0.5mmol bissulfonate acidic ionic liquid to a 100mL single-necked flask with a stirring bar and a reflux condenser. Reflux reaction for 3 hours under vigorous stirring, cooling, suction filtration, recrystallization of filter residue with 95% ethanol, vacuum drying to obtain pure 9-phenyl-1,8-dioxo-1,2,3,4,5,6, 7,8,9,10-Decahydroacridine, the yield is 90%. The bissulfonate acidic ionic liquid catalyst and a small amount of unreacted raw materials contained in the filtrate can be reused without treatment.
Embodiment 2
[0021] Add 10mmol 4-methoxybenzaldehyde, 20mmol 1,3-cyclohexanedione, 30mmol ammonium acetate, 30mL absolute ethanol and 0.5mmol bissulfonate acidic ionic liquid to a 100mL vessel equipped with a stirring bar and a reflux condenser In a one-mouth bottle. Reflux reaction for 2.5h under vigorous stirring, cooling, suction filtration, recrystallization of filter residue with 95% ethanol, vacuum drying to obtain pure 9-(4-methoxyphenyl)-1,8-dioxo-1,2,3 , 4,5,6,7,8,9,10-decahydroacridine, the yield was 94%. The filtrate contains bissulfonate acidic ionic liquid catalyst and a small amount of unreacted raw materials, which can be reused without treatment.
Embodiment 3
[0023] Add 10mmol benzaldehyde, 25mmol 5,5-dimethyl-1,3-cyclohexanedione, 40mmol ammonium acetate, 35mL absolute ethanol and 0.7mmol bissulfonate acidic ionic liquid to 100mL with stirring bar and reflux Condenser in a one-necked bottle. Reflux reaction for 4.5h under vigorous stirring, cooling, suction filtration, recrystallization of filter residue with 95% ethanol, vacuum drying to obtain pure 3,3,6,6-tetramethyl-1,8-dioxo-9-phenyl -1,2,3,4,5,6,7,8,9,10-Decahydroacridine in 91% yield. The filtrate contains bissulfonate acidic ionic liquid catalyst and a small amount of unreacted raw materials, which can be reused without treatment.
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Abstract
The invention provides a method for preparing 9-aryl multi-hydrogen acridine ramification through catalysis, and belongs to the technical field of organic chemical industry. The method is as follows: the mole ratio of aromatic aldehyde, 1,3-cyclohexanedione ramification and ammonium acetate is 1:(2-3):(3-5), the molar weight of a di-sulfonic acid group acidic ionic liquid catalyst accounts for 3%-8% of the used aromatic aldehyde and the usage amount of reaction solvent anhydrous ethanol accounts for 60%-90% of the total weight of a material in a reaction used for preparing the 9-aryl multi-hydrogen acridine ramification and comprises the following steps of: carrying out a reflux reaction for 3-7 hours, wherein reaction pressure is 1 barometric pressure; cooling after the reaction is completed; carrying out suction filtration; recrystallizing filter residues by using 95% ethanol; and carrying out vacuum drying to obtain the pure 9-aryl multi-hydrogen acridine ramification, wherein the di-sulfonic acid group acidic ionic liquid catalyst contained in filter liquor and a small quantity of unreacted raw materials can be reused without being treated. Compared with other preparation methods, the method provided by the invention has the characteristics of high catalytic activity, small catalyst usage amount, catalyst recycling, simpleness and convenience for the integral process, and the like.
Description
technical field [0001] The invention belongs to the technical field of organic chemical industry, in particular to a method for catalytically preparing 9-aryl polyhydroacridine derivatives. Background technique [0002] 1,4-Dihydropyridine compounds constitute a class of important calcium ion channel regulators, which have the effect of treating heart rhythm disorders. The 9-aryl polyhydroacridine derivatives have a 1,4-dihydropyridine ring structure, have important physiological activities, and are intermediates for the synthesis of various drugs. Therefore, studying the preparation of such compounds has become a common concern of many chemists. [0003] Acidic ionic liquids, especially Bronster acidic ionic liquids, which are easy to prepare and stable to water and air, are green and pollution-free, have good solubility for organic and inorganic compounds, uniformly distributed acidic sites, and are easy to produce The advantages of separation and recycling are applied i...
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