Method for preparing 3-nitropropionic acid

A technology of nitropropionic acid and ethyl nitropropionate, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high production cost and expensive reagents

Inactive Publication Date: 2015-03-25
QUFU DELU BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0021] Although these two methods are simple to operate, the production cost is ...

Method used

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  • Method for preparing 3-nitropropionic acid
  • Method for preparing 3-nitropropionic acid
  • Method for preparing 3-nitropropionic acid

Examples

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Embodiment 1

[0045] Embodiment 1: comprise the steps:

[0046] 1) Preparation of bromopropionic acid 4：

[0047] Add acrylic acid (162 g, 2.25 mol) and 47% HBr (400 g, 2.32 mol) into a 1L four-necked flask, and heat to reflux for 4 h. The water dispenser evaporates most of the water in the solution, and stops heating when the temperature reaches 130°C. Cool to form a white solid, add water to dissolve, extract with EA (150 ml×3), combine the organic phases to dry over anhydrous sodium sulfate, and distill under reduced pressure to obtain 308 g of white solid with a yield of 90%.

[0048] 2) Preparation of ethyl 3-bromopropionate 3 :

[0049] 3-bromopropionic acid 4 (15 g, 100 mmol) was added to 200 ml of ethanol, under stirring, 2 droppers of concentrated sulfuric acid were added, and heated to reflux for 6 h. Ethanol was distilled off under reduced pressure, sulfuric acid was washed away by adding 150 ml of water, extracted with EA (200 ml×3), the organic phases were combined,...

Embodiment 2

[0054] Example 2: The difference from the examples is the difference in step 4): 3-ethyl nitropropionate2 (1 g, 6.8 mmol) to 10 ml THF+HO 2 O, LiOH was added in batches at room temperature for 5 h. Water was added and extracted with EA (100 ml×3), the organic phases were combined and dried over anhydrous sodium sulfate, distilled under reduced pressure, and 0.26 g of white solid was obtained by silica gel column chromatography, with a yield of 33%.

[0055]

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Abstract

The invention discloses a method for preparing 3-nitropropionic acid. Acrylic acid serves as a raw material, and the 3-nitropropionic acid is prepared by the following four steps: performing olefin addition, performing esterification, carrying out an SN2 reaction and hydrolyzing. Compared with the other methods, the method has the advantages of readily available raw materials, low price, simplicity in operation, mild and controllable conditions, high yield and the like.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a preparation method of 3-nitro propionic acid. technical background [0002] The structural formula of 3-nitropropionic acid is as formula 1, [0003] [0004] 1 [0005] 3-Nitropropionic acid is a very useful organic chemical intermediate, which can be used in the synthesis of β-amino acids. [0006] In addition, it has recently been found that 3-nitropropionic acid has a protective effect on dopaminergic nerves, thereby achieving the effect of preventing Parkinson's disease. It is mainly related to reducing the generation of malondialdehyde, stimulating the synthesis of reduced glutathione, and protecting dopamine neurons. In addition, 3-nitropropionic acid preconditioning can induce cerebral ischemic tolerance and exert a protective effect on focal ischemia-reperfusion injury. It may be related to reducing the permeability of the blood-brain bar...

Claims

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Application Information

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IPC IPC(8): C07C205/51C07C201/12
Inventor 刘涛姚雷
Owner QUFU DELU BIOTECH
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