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Method for preparing 2-arylimidazo [2,1-alpha] isoquinoline

A kind of arylimidazo, isoquinoline technology, applied in the direction of organic chemistry and the like, can solve the problems of serious environmental pollution, unsuitable for industrial production and the like, and achieves the effects of few reaction steps, low cost and little pollution

Inactive Publication Date: 2008-11-19
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the third step of the synthetic method disclosed in Chinese patent CN1872855, because potassium nitrite, acetic anhydride, dimethyl sulfoxide and other compounds and solvents are used, nitrogen oxide gas is generated in the reaction process, so the environmental pollution is more serious. Suitable for industrial production

Method used

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  • Method for preparing 2-arylimidazo [2,1-alpha] isoquinoline
  • Method for preparing 2-arylimidazo [2,1-alpha] isoquinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1) Add 110 grams (1.0 mol) of m-xylbenzene in a round bottom flask with mechanical stirring, AlCl 3 135 g (1.0 mol), 150 ml of petroleum ether at 60-90°C, and 101 g (1.3 mol) of acetyl chloride were added dropwise. The reaction was incubated at room temperature for 15 minutes to form a solid. Add 200 ml of water to the reaction mixture, pour the pot liquid into a 1000 ml beaker, add an appropriate amount of water, separate the petroleum ether layer, and extract the water layer with an appropriate amount of petroleum ether. The petroleum ether liquids were combined, the solvent was evaporated to dryness, and 20 cm Vickers tube was used to rectify under reduced pressure to obtain 135 g of 95.5% (GC) product 2,4-dimethylacetophenone, with a yield of 87%.

[0023] 2) 20.15 grams (0.13mol) of 4-dimethylacetophenone and 140 milliliters of methanol are dropped into a round-bottomed flask with mechanical stirring, and after stirring and dissolving, 21.5 grams (0.13mol) of liqu...

Embodiment 2

[0028] 1) Add AlCl to a round bottom flask with mechanical stirring 3 135 g (1.0 mol), 101 g (1.3 mol) of acetyl chloride and 400 ml of dichloromethane, and 110 g (1.0 mol) of m-xylbenzene was added dropwise at 0°C. The reaction was incubated at room temperature for 40 minutes. 400 ml of water was added to the reaction mixture, the dichloromethane layer was separated, and the aqueous layer was extracted with an appropriate amount of dichloromethane. Dichloromethane was combined, the solvent was evaporated to dryness, and 20 cm Vickers tube was used for rectification under reduced pressure to obtain 130 g of 95.5% (GC) product 2,4-dimethylacetophenone, with a yield of 84%.

[0029] Step 2) is the same as step 2) in Example 1.

[0030] 3) Add 12.40 grams (0.32mol) of sodium amide powder and 300 milliliters of o-xylene in a 500 milliliter three-necked flask, and dissolve 6.88 grams (0.053 mol) of isoquinoline in 100 milliliters of o-xylene while stirring at 130° C. The soluti...

Embodiment 3

[0033] 1) Add 120 grams (1.0 mol) of n-propylbenzene, AlCl 3135 g (1.0 mol), 150 ml of petroleum ether at 60-90°C, and 101 g (1.3 mol) of acetyl chloride were added dropwise. The reaction was incubated at room temperature for 15 minutes to form a solid. Add 200 ml of water to the reaction mixture, pour the pot liquid into a 1000 ml beaker, add an appropriate amount of water, separate the petroleum ether layer, and extract the water layer with an appropriate amount of petroleum ether. The petroleum ether liquids were combined, the solvent was evaporated to dryness, and 146 g of the product 4-n-propylacetophenone was obtained by vacuum distillation with a 20 cm Vickers tube, with a yield of 90%.

[0034] 2) Put 21.0 grams (0.13mol) of 4-n-propyl acetophenone and 140 milliliters of methanol into a round-bottomed flask with mechanical stirring. After stirring and dissolving, add 21.5 grams (0.13mol) of liquid bromine dropwise and dissolve in 60 milliliters of methanol The soluti...

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Abstract

This invention relates to a method of preparing 2 - aryl imidazo- [ 2, 1 - a] isoquinoline. It takes isoquinoline as raw material to synthesize amino isoquinoline; takes substituted benzene as raw material to synthesize substituted phenylethylketone, by bromination to generate Alpha -brom substituted phenylethylketone, then takes reaction with amido isoquinoline generated by above step to prepare 2 - aryl imidazo- [ 2, 1 - a] isoquinoline.

Description

technical field [0001] The invention relates to a synthesis method of 2-aryl imidazo[2,1-a]isoquinoline. Background technique [0002] Family planning is a basic national policy of our country, and the research and development of anti-early pregnancy drugs has practical significance to the development of our country's economy and society. Most of the drugs used for emergency contraception and abortion are steroids and prostaglandin compounds. Later found that some non-steroidal compounds also have similar pregnancy termination activity [Toja, E.; Omodei-sale, A.; Cattaneo, C.; Galliani, G.Eur.J.Med.Chem.1982,17,223 . Winters, G.; Odasso, G.; Conti, M.; Tarzia, G.; Galliani, G. Eur. J. Med. Chem. 984, 19, 215.]. [0003] Chinese patent ZL99102522.9 discloses two non-steroidal compounds with anti-early pregnancy activity, which were published in Shang Zhicai [Shang, Z.C.; Hu, G.X.; Wu, T.X.; Fang, Y.Y.; Yu, Q.S. Chinese Journal of Chemistry, 2004, 22, 315-320.] and Chinese ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 骆成才张华星杨志杰
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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