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Green synthesis method of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-ketone

A diethylamino, green synthesis technology, applied in the direction of chemical instruments and methods, molecular sieve catalysts, physical/chemical process catalysts, etc., can solve the problems of pyrrolidine corrosion, low product yield, easy yellowing, etc., to improve conversion efficiency, increase yield and purity, and save input costs

Inactive Publication Date: 2020-06-05
李孝林
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The product yield in this patent embodiment is lower, and the catalyst pyrrolidine used has corrosiveness and flammability and sees light or humid air and easily turns yellow

Method used

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  • Green synthesis method of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-ketone
  • Green synthesis method of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-ketone
  • Green synthesis method of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-ketone

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Synthesis of 2-(4-(diethylamino)phenyl)-3-hydroxyl-6-nitro-4-ketone: 4-(diethylamino)benzaldehyde (3.54g, 0.02mol) and 2-hydroxy -5-Nitroacetophenone (3.80g, 0.021mol) was used as the reaction raw material, heated to 120°C for 5h, after the reaction, the reaction solution was naturally cooled down to 60°C, 10g of absolute ethanol was added to make a slurry for 15min, suction filtered, and the residue Wash with 5g of absolute ethanol and dry at 60°C for 12h to obtain 5.61g of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-one with a yield of 78.8% and a purity of 99.2% , ES: [M+1] + 357.14.

Embodiment 2

[0039] The difference between Example 2 and Example 1 is that the heating temperature is set to 130°C.

[0040] Synthesis of 2-(4-(diethylamino)phenyl)-3-hydroxyl-6-nitro-4-ketone: 4-(diethylamino)benzaldehyde (3.54g, 0.02mol) and 2-hydroxy -5-Nitroacetophenone (3.80g, 0.021mol) was used as the reaction raw material, heated to 130°C for 5h, after the reaction, the reaction solution was naturally cooled down to 60°C, 10g of absolute ethanol was added to make a slurry for 15min, suction filtered, and the residue Wash with 5g of absolute ethanol and dry at 60°C for 12h to obtain 5.68g of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-one with a yield of 79.8% and a purity of 99.1% .

Embodiment 3

[0042] The difference between embodiment 3 and embodiment 1 is that nickelocene is added as a catalyst.

[0043]Synthesis of 2-(4-(diethylamino)phenyl)-3-hydroxyl-6-nitro-4-ketone: 4-(diethylamino)benzaldehyde (3.54g, 0.02mol) and 2-hydroxy -5-Nitroacetophenone (3.80g, 0.021mol) was used as the reaction raw material, and nickelocene (calculated as nickel, 0.06g, 0.001mol) was added, heated to 120°C for 5h, and the reaction liquid was naturally cooled after the reaction To 60°C, add 10g of absolute ethanol to make slurry for 15min, filter with suction, wash the filter residue with 5g of absolute ethanol, and dry at 60°C for 12h to obtain 6.43g of 2-(4-(diethylamino)phenyl)-3-hydroxy- 6-nitro-4-one, yield 90.3%, purity 99.2%.

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Abstract

The invention discloses a green synthesis method of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-ketone, and relates to the technical field of organic synthesis. The preparation method comprises thefollowing steps: taking 4-(diethylamino)benzaldehyde and 2-hydroxy-5-nitroacetophenone as reaction raw materials, heating to carry out reactions, naturally cooling the reaction solution after reactions, adding ethanol, pulping, carrying out suction filtration, washing filter residues with ethanol, and drying to obtain 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-one. 4-(diethylamino)benzaldehyde and 2-hydroxy-5-nitroacetophenone carry out reactions in a molten state; the use of a reaction solvent is avoided, the investment cost of a reaction solvent is saved, moreover, the amount of wastewater generated in post-treatment is reduced, the synthesis method becomes more environmentally friendly, and meanwhile, the yield and purity of 2-(4-(diethylamino)phenyl)-3-hydroxy-6-nitro-4-ketone areimproved.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a green synthesis method of 2-(4-(diethylamino)phenyl)-3-hydroxyl-6-nitro-4-one. Background technique: [0002] Flavonoids are a class of compounds that exist in nature and have a 2-phenylchromone structure. The molecule contains a ketone carbonyl group. The oxygen atom at the first position is basic and can form a salt with a strong acid. Its hydroxyl group is derived from Things are mostly yellow. Flavonoids are usually combined with sugars to form glycosides in plants, and a small part exists in free form. There are many compounds with medicinal value in flavonoids. These compounds are used to prevent and treat cardiovascular and cerebrovascular diseases, such as reducing the fragility of blood vessels, improving the permeability of blood vessels, reducing blood lipids and cholesterol, and preventing and treating elderly hypertension, cerebral hemorrhage, and coron...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/62B01J29/03B01J29/04
CPCB01J29/0308B01J29/0333B01J29/041B01J29/044B01J2229/186C07D311/62
Inventor 李孝林
Owner 李孝林