Method for producing triketone compound
A manufacturing method and compound technology, which are applied in the field of manufacture of triketone compounds to achieve the effect of high yield
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Embodiment 1
[0255] Production of 3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-(4-methoxyphenyl)quinoxalin-2(1H)-one (1a)
[0256] [chemical 10]
[0257]
[0258] Add 1-(4-methoxyphenyl)-2-oxo A solution of 5.0 g (16 mmol) of 1,2-dihydroquinoxaline-3-carboxylic acid chloride in 10 mL of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours, washed with 10% hydrochloric acid, and the separated organic layer was dried with anhydrous sodium sulfate. Inorganic substances were filtered off, and 2.1 g (21 mmol) of triethylamine was added to the obtained solution, followed by stirring at room temperature for 3 hours. After washing the reaction mixture with 10% hydrochloric acid, the organic layer after separation was dried with anhydrous sodium sulfate. Inorganic substances were filtered off, and the solvent was distilled off under reduced pressure, and the residue was recrystallized from methanol to obtain 3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-(4 -Methoxyp...
Embodiment 2
[0263] Production of 5-chloro-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-(4-methoxyphenyl)quinoxalin-2(1H)-one (1b)
[0264] [chemical 11]
[0265]
[0266] Add 5-chloro-1-(4-methoxyphenyl) dropwise to 1.7 g (15.0 mmol) of 1,3-cyclohexanedione and 3.2 g (31.5 mmol) of triethylamine in 8 mL of chlorobenzene at room temperature A solution of 5.0 g (14.3 mmol) of )-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid chloride in 18 mL of chlorobenzene. The reaction mixture was stirred at room temperature for 2 hours, and then 22 mL of chlorobenzene was added to the reaction mixture, followed by washing with 10% hydrochloric acid. The organic layer after liquid separation was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with acetone to obtain 5-chloro-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-(4-methoxyphenyl)quinoxaline as a yellow powder -2(1H)-one 4.9 g. (yield 81%)
[0267] Melting point: 249-251°C ...
Embodiment 3
[0271] Production of 5-chloro-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-(4-methoxyphenyl)quinoxalin-2(1H)-one (1b)
[0272] 5-Chloro-1-(4-methoxyphenyl) was added dropwise to a solution of 1.7 g (15.0 mmol) of 1,3-cyclohexanedione and 1.6 g (15.7 mmol) of triethylamine in 5 mL of toluene at room temperature - A solution of 5.0 g (14.3 mmol) of 2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid chloride in 17 mL of toluene. To the reaction mixture was further added 1.6 g (15.7 mmol) of triethylamine, followed by stirring at 60° C. for 2 hours. 11 mL of toluene was added to the reaction mixture, followed by washing with 10% hydrochloric acid. The organic layer after liquid separation was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with acetone and water to obtain 5-chloro-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-(4-methoxyphenyl)quinone as a yellow powder Oxaline-2(1H)-one 4.9 g. (yield 81%)
[0273]...
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