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Preparation method for 4-pyridinecarboxaldehyde

A technology of pyridinecarboxaldehyde and pyridine, which is applied in the field of preparation of 4-pyridinecarboxaldehyde, can solve the problems of expensive raw materials, low yield and high price of the modified method, and achieves the effects of low raw material price, simple preparation process and short preparation time.

Inactive Publication Date: 2017-03-22
安徽省诚联医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 4-pyridinecarbaldehyde is an important product of organic synthesis reagents, and the synthesis methods of 4-pyridinecarbaldehyde include the following: (1) 4-picoline oxidation synthesis, such as Catalysis Today, 91-92, 7-11; 2004 , CN101898999 and other reports, this method has many by-products and low yield; (2) oxidative synthesis with 4-pyridinemethanol as raw material, this method is currently the main method for synthesizing 4-pyridinecarbaldehyde, and the yield is high, such as Synthesis, (11), 868-71; 1988, Synthesis, (11), 868-71; 1988, etc., although the yield of this method is high, but the raw material 4-pyridinemethanol is expensive, making the price of 4-pyridinecarbaldehyde higher; (3) Synthesis of 4-pyridinecarbaldehyde by reduction of 4-pyridinecarbonitrile, such as: CN 103044320, etc. The yield of this method is relatively high, but the raw materials and cost of the modified method are relatively high; (4) Selectivity of 4-pyridinecarbohydrazide Oxidative synthesis of 4-pyridinecarbaldehyde, such as: Chemistry Letters, 39(6), 546-547; 2010, but the catalyst is more expensive, the yield is lower, and the cost is higher; (5) Reduction of isonicotinic acid and its esters, Such as Science of Synthesis, 25, 563-574; 2007, Bulletin of the Chemical Society of Japan, 74(10), 1803-1815; 2001, Acts Chem. Scand., 17(4), 972-8; 1963, etc., the The reducing agent of the method is expensive and the cost is high; (6) 4-vinylpyridine oxidation, Eur. Pat.Appl., 147593, 10 Jul 1985, CN2006 1800132, the yield of this method is not high, and the cost is high
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Method used

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Embodiment 1

[0013] A kind of preparation method of 4-pyridinecarbaldehyde, concrete steps are as follows:

[0014] Step 1: Add 26 g of isonicotinic acid to 13.2 g of ethylenediamine and raise the temperature to 150 degrees Celsius for 5 hours, then raise the temperature to 200 degrees Celsius for 3 hours, then raise the temperature to 260 degrees Celsius for 3 hours, cool to room temperature, add ethyl acetate for recrystallization to obtain 4-pyridine-2-imidazoline 25.6g, the yield is 87%;

[0015] Step 2, dissolve 14.7 g of 4-pyridine-2-imidazoline in 40 ml of absolute ethanol, cool to minus 10 degrees Celsius under nitrogen protection and ice bath, add 3 g of sodium metal in batches, and keep the temperature during the addition Do not exceed minus 5 degrees Celsius, react for 1 hour, after the reaction, remove absolute ethanol and add an oxalic acid solution with a pH of 1-2, heat and reflux for 2 hours, after the reaction, add sodium bicarbonate to adjust the solution to be alkaline, ...

Embodiment 2

[0017] A kind of preparation method of 4-pyridinecarbaldehyde, concrete steps are as follows:

[0018] Step 1: Add 26 g of isonicotinic acid to 23.76 g of o-phenylenediamine, raise the temperature to 160 degrees Celsius for 4 hours, then raise the temperature to 200 degrees Celsius for 3 hours, then raise the temperature to 260 degrees Celsius for 3 hours, cool to room temperature, add ethyl acetate to carry out Crystallization obtained 33 g of 4-pyridine-2-benzimidazoline, with a yield of 84%;

[0019] Step 2, dissolve 0.1mol 4-pyridine-2-benzimidazoline in 40 ml of absolute ethanol, cool to minus 10 degrees Celsius under nitrogen protection and ice bath, add 2 g of sodium borohydride in batches, and keep The temperature does not exceed minus 5 degrees Celsius, react for 2 hours, after the reaction, add ammonium chloride to quench the unreacted sodium borohydride, remove absolute ethanol and add oxalic acid solution with a pH of 2, heat and reflux for 2 hours, after the react...

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Abstract

The invention discloses a preparation method for 4-pyridinecarboxaldehyde. The preparation method specifically comprises the following steps that firstly, a solvent-free reaction is conducted, specifically, isonicotinic acid and ethylenediamine or o-diaminobenzene are reacted under the solvent-free condition to synthesize 4-pyridine-2-imidazoline; and secondly, reductive hydrolysis is conducted, specifically, the synthesize 4-pyridine-2-imidazoline is subjected to reductive hydrolysis to synthesize the 4-pyridinecarboxaldehyde. The method is wide in raw material source, low in raw material cost and production cost, simple in preparation process, suitable for large-scale industrial production, little in by-product, short in preparation time, high in yield and good in production effect.

Description

technical field [0001] The invention relates to the field of reagent production, in particular to a preparation method of 4-pyridinecarbaldehyde. Background technique [0002] 4-pyridinecarbaldehyde is an important product of organic synthesis reagents, and the synthesis methods of 4-pyridinecarbaldehyde include the following: (1) 4-picoline oxidation synthesis, such as Catalysis Today, 91-92, 7-11; 2004 , CN101898999 and other reports, this method has many by-products and low yield; (2) oxidative synthesis with 4-pyridinemethanol as raw material, this method is currently the main method for synthesizing 4-pyridinecarbaldehyde, and the yield is high, such as Synthesis, (11), 868-71; 1988, Synthesis, (11), 868-71; 1988, etc., although the yield of this method is high, but the raw material 4-pyridinemethanol is expensive, making the price of 4-pyridinecarbaldehyde higher; (3) Synthesis of 4-pyridinecarbaldehyde by reduction of 4-pyridinecarbonitrile, such as: CN 103044320, et...

Claims

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Application Information

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IPC IPC(8): C07D213/48
CPCC07D213/48
Inventor 刘辉
Owner 安徽省诚联医药科技有限公司
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