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Method for preparing 2H-isoquinoline-1-ketones

A ketone compound and isoquinoline technology is applied in the field of preparation of 2H-isoquinoline-1-one compounds, and can solve the problems of easy spontaneous combustion of diisobutylaluminum hydride, expensive and unobtainable raw materials, harsh reaction conditions and the like , to achieve the effect of short reaction time, simple operation and mild reaction conditions

Inactive Publication Date: 2011-10-19
SHANGHAI YISHI CHEM TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The disadvantage of this method is that the raw materials are expensive and difficult to obtain, and diisobutyl aluminum hydride is prone to spontaneous combustion and danger in the air, and the reaction temperature is a low temperature condition of -78 degrees, and the harsh reaction conditions are difficult to achieve

Method used

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  • Method for preparing 2H-isoquinoline-1-ketones
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  • Method for preparing 2H-isoquinoline-1-ketones

Examples

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Embodiment 1

[0023] Embodiment 1: Synthesis of 5-bromo-2H isoquinolin-1-one

[0024] 2-Bromocinnamic acid (41.7g, 0.183mol), triethylamine (7.44g, 73.64mmol) were dissolved in 300mL toluene and stirred at room temperature for 30 minutes. Diphenylphosphoryl azide DPPA (50.5 g, 0.138 mol) was added to the above reaction solution and the reaction was continued at room temperature for 2 hours, and the reaction of the raw materials was followed by thin layer chromatography (TLC). The reaction solution was diluted with 500 mL of ethyl acetate, and the organic phase was washed successively with 100 mL of 5% aqueous sodium hydroxide solution, 500 mL of water and 200 mL of saturated brine. The organic layer was dried with anhydrous sodium sulfate, and evaporated to dryness under reduced pressure by rotary evaporation to obtain 43.3 g of an azide intermediate with a yield of 95%. The above-mentioned azide intermediate (43.342g, 0.172mol) was dissolved in 200mL of diphenyl ether, and then 20.6mL of ...

Embodiment 2

[0026] Example 2: Synthesis of 5-trifluoromethoxy-2H isoquinolin-1-one

[0027] 2-Trifluoromethoxycinnamic acid (4.76 g, 20.50 mmol), triethylamine (2.07 g, 20.50 mmol) were dissolved in 50 mL of toluene and stirred at room temperature for 30 minutes. DPPA (5.63g, 20.50mmol) was added to the above reaction solution and the reaction was continued at room temperature for 2 hours, and the reaction of the raw materials was followed by TLC. The reaction solution was diluted with 100 mL of ethyl acetate, and the organic phase was washed successively with 20 mL of 5% aqueous sodium hydroxide solution, 50 mL of water and 20 mL of saturated brine. The organic layer was dried with anhydrous sodium sulfate, and evaporated to dryness under reduced pressure by rotary evaporation to obtain 4.8 g of an azide intermediate with a yield of 90%. The above-mentioned azide intermediate (4.7g, 18.27mmol) was dissolved in 30mL of diphenyl ether, and then 6mL of N,N-diisopropylethylamine was added d...

Embodiment 3

[0029] Example 3: Synthesis of 7-methoxy-2H isoquinolin-1-one

[0030] 4-Methoxycinnamic acid (5 g, 28.05 mmol), triethylamine (2.83 g, 28.05 mmol) were dissolved in 50 mL of toluene and stirred at room temperature for 30 minutes. DPPA (7.72g, 28.05mmol) was added to the above reaction solution, and the reaction was continued at room temperature for 2 hours, and TLC traced that the reaction of the raw materials was complete. The reaction solution was diluted with 100 mL of ethyl acetate, and the organic phase was washed successively with 20 mL of 5% aqueous sodium hydroxide solution, 50 mL of water and 20 mL of saturated brine. The organic layer was dried with anhydrous sodium sulfate, and evaporated to dryness under reduced pressure by rotary evaporation to obtain 5 g of azide intermediate with a yield of 90%. The above-mentioned azide intermediate (5.87g, 28.05mmol) was dissolved in 30mL of diphenyl ether, and then 14mL of N,N-diisopropylethylamine was added dropwise. After...

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Abstract

The invention discloses a method for preparing 2H-isoquinoline-1-ketones, which comprises the steps of taking corresponding cinnamic acid derivatives and diphenylphosphoryl azide (DPPA) as raw materials, synthesizing nitrine intermediates under the existence of organic base, and carrying out reaction under the conditions of the organic base and a proper solvent as well as proper temperature. Compared with other methods, the method for preparing the 2H-isoquinoline-1-ketones has the advantages of high yield, short reaction time, environment friendliness, simplicity in operation, low cost and the like, thus not only being suitable for small-scale synthesis in a laboratory, but also being suitable for industrial enlargement production. The prepared 2H-isoquinoline-1-ketones can be used for screening of bioactivity or research and development of new drugs.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, in particular to a preparation method of 2H-isoquinolin-1-one compounds. technical background [0002] 2H-isoquinolin-1-one compounds are a class of important pharmaceutical intermediates, and its structural formula is shown in formula I: [0003] [0004] Wherein the R substituent can be 2-Cl, 3-Cl, 4-Cl, 2-Br, 3-Br, 4-Br, 2-Me, 3-Me, 4-Me, 2-MeO, 3-MeO, 4-MeO, 2-CN, 3-CN, 4-CN, 2-CF 3 , 3-CF 3 , 4-CF 3 , 2-OCF 3 , 3-OCF 3 , 4-OCF 3 . [0005] At present, there are mainly three ways to prepare such compounds reported in the literature. First, cinnamic acid generates acid chloride under the action of oxalyl chloride, and the acid chloride reacts with sodium azide in acetone solution to form an azide intermediate, and the azide intermediate and mercury acetate are refluxed in o-dichlorobenzene for 14 hours to obtain H-iso Quinolin-1-one [Journal of the Chinese Chemical Societ...

Claims

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Application Information

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IPC IPC(8): C07D217/24
Inventor 崔振伟李雷刘文岗薛旭婷
Owner SHANGHAI YISHI CHEM TECH
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