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Preparation method of isopropyl 2-(3-nitrobenzal) acetoacetate

A technology of isopropyl acetoacetate and isopropyl acetate, applied in the field of preparation of isopropyl 2-acetoacetate, can solve the problems of polluted environment, a large amount of acidic waste water, large amount of concentrated acid, etc. The effect of production costs

Active Publication Date: 2013-11-27
BEIJING RED SUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When concentrated sulfuric acid is used as a catalyst, there is a large amount of concentrated acid used, and a large amount of acidic wastewater will be generated during post-treatment, which seriously pollutes the environment.

Method used

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  • Preparation method of isopropyl 2-(3-nitrobenzal) acetoacetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Take seven 500ml three-neck round bottom flasks, add 145ml of isopropyl acetoacetate respectively, cool to 0°C, stir and add concentrated sulfuric acid 6, 7, 8, 9, 10, 11 and 12ml dropwise respectively, and add in batches A total of 74.8g of nitrobenzaldehyde was stirred and reacted for 1 hour at 5°C. 0 degrees for 12 hours. Suction filtration, washing with purified water to neutrality, drying and separation of crude products. Dissolve the crude product in 100ml of isopropanol, stir and heat to 50°C, and keep it warm for 5 hours. Cool down, crystallize for 6 hours, filter with suction, and dry to obtain white solids 1-7, respectively.

Embodiment 2

[0011] Take four 500ml three-neck round bottom flasks, add 72.5, 145, 217.5, 290, 362.5ml of isopropyl acetoacetate respectively, cool to 4 degrees, stir and add 10ml of concentrated sulfuric acid dropwise, add m-nitrobenzene in batches A total of 74.8g of formaldehyde was stirred and reacted at 8 degrees for 12 hours. Place it at 10 degrees for 72 hours. Suction filtration, washing with alkaline aqueous solution until neutral, and drying to obtain the crude product. Dissolve the crude product in 200ml of isopropanol, stir and heat to 89°C, and keep it warm for 1 hour. Cool down, crystallize for 24 hours, filter with suction, and dry to obtain white solid 8-11.

Embodiment 3

[0013] Take three 5-liter three-necked flasks, add 1450ml of isopropyl acetoacetate, cool to 2 degrees, stir and add 90, 100, 110ml of concentrated sulfuric acid dropwise, add 748g of m-nitrobenzaldehyde in batches, and stir at 7 degrees for 1 hour . 0 degrees for 48 hours. Suction filtration, washed with purified water until neutral, dried to obtain the crude product. Dissolve the crude product in 1500ml of isopropanol, stir and heat to 80°C, and keep it warm for 3 hours. Cool down, crystallize for 18 hours, filter with suction, and dry to obtain white solids 12-15, respectively.

[0014] The productive rates of Examples 1, 2 and 3 are shown in Table 1.

[0015] Table 1

[0016]

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PUM

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Abstract

The invention discloses a preparation method of isopropyl 2-(3-nitrobenzal) acetoacetate. The method comprises the step of: reacting m-nitrobenzaldehyde with isopropyl acetoacetate in the presence of concentrated sulfuric acid as a catalyst to generate isopropyl 2-(3-nitrobenzal) acetoacetate, wherein the molar ratio of m-nitrobenzaldehyde to isopropyl acetoacetate to concentrated sulfuric acid is 1:(1-5):(0.26-0.41). The preparation method of isopropyl 2-(3-nitrobenzal) acetoacetate disclosed by the invention has low catalyst consumption and high yield.

Description

technical field [0001] The invention relates to a preparation method of 2-(3-nitrobenzylidene) isopropyl acetoacetate. Background technique [0002] Hypertension is a common disease that affects human health, and the development of antihypertensive drugs has always been the focus of drug development. As a new type of dihydropyridine calcium channel blocker, azedipine is widely used clinically in the treatment of various hypertensive patients. It has the advantages of high selectivity, strong and long-lasting antihypertensive effect, and little impact on the heart. It also shows good anti-atherosclerosis and protective effects on the kidney and heart. It is a drug for the treatment of hypertension with good application prospects. . [0003] As an important intermediate in the synthesis of azedipine molecules, a large amount of catalysts need to be used in the synthesis process of 2-(3-nitrobenzylidene) isopropyl acetoacetate. When concentrated sulfuric acid is used as a ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/56C07C201/12
Inventor 马德君
Owner BEIJING RED SUN PHARMA
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