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Preparation method of 2-chloro nicotinaldehyde

A technology of nicotinic aldehyde and chloronicotinic acid, applied in the direction of organic chemistry and other directions, can solve the problems of blank in industrial synthesis and large-scale production, no value of industrial production, expensive reaction reagents, etc., and achieves low cost of raw materials, mild reaction conditions, and ease of use. The effect of purification

Inactive Publication Date: 2015-04-01
SUZHOU JONATHAN NEW MATERIALS TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthetic method of 2-chloronicotinaldehyde has few bibliographical reports, and there are various defects in the reported method, for example, the reaction reagent is expensive, the yield is low, and there is basically no value for industrialized production
[0003] The 2-chloronicotinaldehyde currently on the market only has reagent products in small packages, and the price is very expensive. The industrial synthesis and large-scale production of this product are still blank in the market

Method used

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  • Preparation method of 2-chloro nicotinaldehyde
  • Preparation method of 2-chloro nicotinaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0015] (1) Synthesis of 2-chloronicotinol

[0016] Add NaBH to the four-neck flask 4 (72g) and tetrahydrofuran 450ml, cooled to -10℃~0℃. Boron trifluoride diethyl ether solution (575g) was added dropwise, and the internal temperature was controlled to be <10°C. After dropping, stirred for 5 minutes. Then add 2-chloronicotinic acid (100g) and tetrahydrofuran 600ml mixed solution dropwise, control the temperature <30°C, after dropping, raise the temperature to room temperature and react for 6h. Adjust the pH to 8-9, filter with suction, extract the filtrate twice with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, filter with suction, and concentrate to obtain 125 g of the product, which is directly used in the next reaction.

[0017] (2) Synthesis of 2-chloronicotinaldehyde

[0018] Add 2-chloronicotinol (125g) and 450ml of dichloromethane into the four-necked bottle, stir evenly, add manganese dioxide (280g), heat up to reflux for 3 hours, after the rea...

Embodiment 2

[0020] (1) Synthesis of 2-chloronicotinol

[0021] Add NaBH to the four-neck flask 4 (80g) and 500ml of tetrahydrofuran, cooled to -10°C to 0°C. Boron trifluoride diethyl ether solution (590g) was added dropwise, and the internal temperature was controlled to be <10°C. After dropping, stirred for 5 minutes. Then add 2-chloronicotinic acid (100g) and tetrahydrofuran 550ml mixed solution dropwise, control the temperature <25°C, after dropping, raise the temperature to room temperature and react for 8h. Adjust the pH to 8-9, filter with suction, extract the filtrate twice with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, filter with suction, and concentrate to obtain 131 g of the product, which is directly used in the next reaction.

[0022] (2) Synthesis of 2-chloronicotinaldehyde

[0023] Add 2-chloronicotinol (131g) and 460ml of dichloromethane into the four-necked bottle, stir well, add manganese dioxide (300g), heat up to reflux reaction for 5h, aft...

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Abstract

The invention provides a preparation method of 2-chloro nicotinaldehyde. A synthetic route which is show in the specification comprises the following steps: (1) reducing a raw material 2-chloronicotinic acid to generate a compound 2; and (2) oxidizing the compound 2 to generate 2-chloro nicotinaldehyde 3. The preparation method of 2-chloro nicotinaldehyde provided by the invention at least has the advantages of mild reaction condition, cheap and easily available raw materials, high yield, easy purification and the like.

Description

technical field [0001] The invention relates to a preparation method of 2-chloronicotinaldehyde, which belongs to the field of synthesis of pharmaceutical intermediates. Background technique [0002] As an important pharmaceutical intermediate, 2-chloronicotinaldehyde is widely used in the pharmaceutical field. The synthesis method of 2-chloronicotinaldehyde is rarely reported in the literature, and the reported method has various defects, such as expensive reagents, low yield, and basically no value for industrial production. [0003] The 2-chloronicotinaldehyde currently on the market only has reagent products in small packages, and the price is very expensive. The industrial synthesis and large-scale production of this product are still blank in the market. With the increasing market demand for 2-chloronicotinaldehyde, people are eager to find a 2-chloronicotinaldehyde synthesis process that can be scaled up industrially. Therefore, the large-scale synthesis and process...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 李卓才李苏杨
Owner SUZHOU JONATHAN NEW MATERIALS TECH
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