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A kind of synthetic method of 3-fluoro-5-nitropyridine-2-carbaldehyde

A synthetic method, nitropyridine technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effect of easy control, simple operation, and short route

Active Publication Date: 2022-05-13
阿里生物新材料(常州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports on the synthesis of 3-fluoro-5-nitropyridine-2-carbaldehyde at present

Method used

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  • A kind of synthetic method of 3-fluoro-5-nitropyridine-2-carbaldehyde
  • A kind of synthetic method of 3-fluoro-5-nitropyridine-2-carbaldehyde

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preparation example Construction

[0021] A kind of synthetic method of 3-fluoro-5-nitropyridine-2-carbaldehyde, this synthetic method comprises the steps:

[0022] (1) According to the mass ratio of compound A and 65% nitric acid with a mass fraction of 3:4~7, and the solid-liquid g / mL ratio of compound A and concentrated sulfuric acid as 1:5, take the material and mix compound A and concentrated sulfuric acid , 65% nitric acid was added dropwise at 20-25°C, and kept for 3-5 hours to obtain compound B;

[0023] (2) According to the mass ratio of compound B and phosphorus pentachloride being 1:2 to 4, and the solid-liquid g / mL ratio of compound B and phosphorus oxychloride being 1:6, the materials were taken, and compound B, oxychloride Add phosphorus into the reactor, set the temperature at 0-3°C, add phosphorus pentachloride, stir, heat to 60°C, and react for 3-6 hours to obtain compound C;

[0024] (3) According to compound C, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane, Pd(dppf)Cl 2 , the mass ratio of ...

Embodiment 1

[0027] A kind of synthetic method of 3-fluoro-5-nitropyridine-2-carbaldehyde, this synthetic method comprises the steps:

[0028] (1) Mix 3g of compound A and 15mL of concentrated sulfuric acid, add 12g of nitric acid with a mass fraction of 65% dropwise at 25°C, keep the reaction for 5 hours, and detect by TLC. After the reaction of the raw materials is completed, the reaction solution is slowly poured into 400mL of ice water, and a yellow solid precipitates out. Filter and dry the filter cake to obtain 3.8 g of compound B. The yield is 90.6%, and the purity is 97.6%;

[0029] (2) Add 1g of compound B and 6mL of phosphorus oxychloride into the reactor, set the temperature at 3°C, add 2g of phosphorus pentachloride, stir, heat to 60°C, react for 6h, TLC detection, the reaction of the raw materials is complete, the reaction solution Pour into 1000mL ice water, extract with ethyl acetate (600mL*4), add saturated sodium bicarbonate to the organic phase very carefully to adjust t...

Embodiment 2

[0034] A kind of synthetic method of 3-fluoro-5-nitropyridine-2-carbaldehyde, this synthetic method comprises the steps:

[0035] (1) Mix 3g of compound A and 15mL of concentrated sulfuric acid, add 12g of nitric acid with a mass fraction of 65% dropwise at 20°C, keep the reaction for 3 hours, TLC detects that the reaction of the raw materials is complete, slowly pour the reaction solution into 400mL of ice water, and a yellow solid precipitates out. Filter and dry the filter cake to obtain 3.7g of compound B with a yield of 88.2% and a purity of 99.1%;

[0036] (2) Add 1g of compound B and 6mL of phosphorus oxychloride into the reactor, set the temperature at 0°C, add 2g of phosphorus pentachloride, stir, heat to 60°C, react for 3 hours, TLC detection, the reaction of the raw materials is complete, and the reaction solution Pour into 1000mL ice water, extract with ethyl acetate (600mL*4), add saturated sodium bicarbonate to the organic phase very carefully to adjust the pH to...

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Abstract

The invention belongs to the technical field of pharmaceutical intermediates, in particular to a method for synthesizing 3-fluoro-5-nitrobenzaldehyde. The present invention uses compound A as a starting material to generate compound B in a concentrated sulfuric acid environment, and compound B undergoes a substitution reaction to generate compound C, which is then combined with 2,4,6-trimethyl-1,3,5,2 , 4,6-trioxatriborinane, etc. react to synthesize compound D, and finally react with selenium dioxide and dioxane to synthesize 3-fluoro-5-nitrobenzaldehyde, and the obtained The yield of the product is high and the purity is high.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, and in particular relates to a synthesis method of 3-fluoro-5-nitropyridine-2-carbaldehyde. Background technique [0002] As an important fine organic chemical intermediate, nitrobenzaldehyde has a wide range of industrial applications and a large demand, and is widely used in pharmaceutical fuels and organic synthesis. At present, the research on the synthesis route of o-nitrobenzaldehyde and p-nitrobenzaldehyde is relatively extensive at home and abroad. In terms of chemical synthesis methods, there are mainly: oxidative nitration method, displacement method, and reduction method. [0003] 3-Fluoro-5-nitrobenzaldehyde is a derivative of nitrobenzaldehyde, which is widely used in medicinal chemistry and organic synthesis. Currently, there are few reports on the synthesis of 3-fluoro-5-nitropyridine-2-carbaldehyde. Therefore, it is necessary to develop a synthetic method th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/12C07C205/44C07D213/61
Inventor 王超金璐怡
Owner 阿里生物新材料(常州)有限公司