Preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol

A quinolinyl and propyne technology is applied in the field of preparation of 3--2-propyn-1-ol, can solve problems such as non-compliance with environmental protection requirements, unfriendly environment, etc., and achieves cost reduction, reaction yield improvement, The effect of reducing harm to the environment

Inactive Publication Date: 2012-11-07
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the above method (document US2003199696A1), the Sonogashira reaction of 3-bromoquinoline and propargyl alcohol needs to use the organic solvent triethylamine as a solvent, which is not environmentally friendly and does not meet environmental protection requirements

Method used

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  • Preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol
  • Preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol

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Effect test

Embodiment 1

[0020] Embodiment 1: Preparation of 3-(3-quinolyl)-2-propyn-1-alcohol:

[0021] In the 100ml reaction flask, add 2g 3-bromoquinoline, 0.8g propargyl alcohol, 0.04g cuprous iodide, 0.07g bis(triphenylphosphine) palladium dichloride (Pd(PPh 3 ) 2 Cl 2 ), 2.8g of potassium carbonate, then add 40ml of water, heat to reflux, and the reaction of raw materials is complete after 40min. Pour the reaction solution into a separatory funnel, extract with 60ml of ethyl acetate, wash the organic layer with 50ml of saturated sodium bicarbonate and 50ml of saturated sodium chloride successively, dry with anhydrous sodium sulfate, filter with suction, and evaporate the filtrate to dryness Yield 1.74 g (98.8%) of solid.

Embodiment 2

[0023] In the 100ml reaction flask, add 2g 3-bromoquinoline, 0.8g propargyl alcohol, 0.4g cuprous iodide, 0.7gPd(PPh 3 ) 2 Cl 2 , 2.8g of potassium carbonate, then add 40ml of water, heat to reflux, 40min after the reaction of raw materials is complete. Pour the reaction solution into a separatory funnel, extract with 60ml of ethyl acetate, wash the organic layer with 50ml of saturated sodium bicarbonate and 50ml of saturated sodium chloride successively, dry with anhydrous sodium sulfate, filter with suction, and evaporate the filtrate to dryness Yield 1.75 g (99.4%) of solid.

Embodiment 3

[0025] In the 100ml reaction flask, add 2g 3-bromoquinoline, 0.8g propargyl alcohol, 0.08g cuprous iodide, 0.07gPd(PPh 3 ) 2 Cl 2 , 2.8g of potassium carbonate, then add 40ml of water, heat to reflux, 40min after the reaction of raw materials is complete. Pour the reaction solution into a separatory funnel, extract with 60ml of ethyl acetate, wash the organic layer with 50ml of saturated sodium bicarbonate and 50ml of saturated sodium chloride successively, dry with anhydrous sodium sulfate, filter with suction, and evaporate the filtrate to dryness Yield 1.73 g (98.3%) of solid.

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Abstract

The invention relates to the technical field of a preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol. According to the preparation method of 3-(3-quinolyl)-2-propyne-1-alcohol, tribromoquinoline reacts with propargyl alcohol in water in the presence of alkali and under the catalysis of palladium and cuprous iodide. According to the invention, water is used as a solvent, and a compound as shown in the formula (II) is prepared by the reaction between a compound as shown in the formula (I) and propargyl alcohol at normal temperature or at the temperature of 15-100 DEG C in the presence of alkali and under the catalysis of palladium and cuprous iodide. By the method, water can be used as a solvent. Therefore, the harm to the environment is minimized, cost is relatively reduced, and reaction yield is also raised.

Description

technical field [0001] The present invention relates to the preparation method of 3-(3-quinolyl)-2-propyn-1-alcohol, specifically, it relates to the reaction of 3-bromoquinoline and propargyl alcohol to prepare 3-(3-quinolyl) - The technical field of the method of 2-propyn-1-ol. Background technique [0002] Preparation of 3-(3-quinolyl)-2-propyn-1-alcohol generally takes 3-bromoquinoline as raw material, which can be prepared by the following method: [0003] 3-bromoquinoline (I) first reacts with propargyl alcohol to obtain formula (II) compound by Sonogashira [0004] [0005] In the above method (document US2003199696A1), the Sonogashira reaction between 3-bromoquinoline and propargyl alcohol requires the use of organic solvent triethylamine as a solvent, which is not environmentally friendly and does not meet environmental protection requirements. Contents of the invention [0006] The purpose of the present invention is to solve the above problems, reduce enviro...

Claims

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Application Information

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IPC IPC(8): C07D215/14
Inventor 毕万福陈旭东单晓燕时惠麟
Owner SHANGHAI INST OF PHARMA IND
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