Substituted furan isoquinolinone derivatives and preparation method thereof
A technology of furan isoquinolinone and derivatives, which is applied in the field of medicinal chemistry, can solve the problems of many by-products, difficult purification, harsh reaction conditions, etc., and achieve the effect of simple steps
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Embodiment 1
[0037] Disperse 1,3-cyclohexanedione and potassium hydroxide uniformly in water, stir at room temperature for 5 minutes, add ethyl chloroacetoacetate in methanol, then stir the system at room temperature for 5 days, and then use 4N Acidify with hydrochloric acid, filter the acidified reaction solution, and the solid obtained is the product: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate. In this step, the molar ratio of 1,3-cyclohexanedione to potassium hydroxide and ethyl chloroacetoacetate is 1:1:1, and the amount of 1,3-cyclohexanedione corresponding to each milliliter of water is 0.1g , The feed amount of ethyl chloroacetoacetate per milliliter of methanol is 0.2g. The yield of this step is 65%. The structure of the resulting product is:
[0038]
[0039] Molecular formula: C 12 H 14 O 4
[0040] Chinese name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate
[0041] English name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate ...
Embodiment 2
[0046] Dissolve ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate and potassium hydroxide in a mixed solvent of methanol and water, and stir the system at room temperature after dissolution Reaction for 5h. Then adjust the pH of the reaction solution to 1 with 6N hydrochloric acid, filter the reaction solution, and the solid obtained by filtration is the product: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2- Formic acid. The mixed solvent used in this step is a 2.5:1 formula of methanol and water. The feed amount of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate per milliliter of mixed solvent is 0.2g. In this step, the molar ratio of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate to potassium hydroxide is 1:6. The yield of this step is 90%. The structure of the resulting product is:
[0047]
[0048] Molecular formula: C 10 H 10 O 4
[0049] Chinese name: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid
[0050] En...
Embodiment 3
[0056] Disperse 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid uniformly in diethylene glycol, add copper powder and pyridine, and then heat the system to 175°C, Keep stirring for 10h. The system was cooled to room temperature, ice water was added, and acidified with 4N hydrochloric acid. The acidified reaction solution was extracted three times with petroleum ether. The combined extract was washed with water once, and then the extract was dried with anhydrous sodium sulfate and spin-dried. The resulting solid is the product: 3-methyl-6,7-dihydrobenzofuran-4-(5H)-one. In this step, the amount of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid corresponding to each milliliter of diethylene glycol is 0.1 g. In this step, the molar ratio of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid to copper powder and pyridine is 1:1:2. The yield of this step was 85%. The structure of the resulting product is:
[0057]
[0058] Molecular formula:...
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