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New preparation method of 5-nitro-salicylaldehyde

A technology of nitrosalicylaldehyde and salicylaldehyde, which is applied in the preparation of nitro compounds, organic chemistry and other directions, can solve the problems such as unfavorable large-scale production of 5-nitrosalicylaldehyde, difficulty in separation and purification, low reaction rate and the like , to achieve the effect of being beneficial to large-scale synthesis, increasing the reaction rate and increasing the yield

Inactive Publication Date: 2012-08-15
OCEAN UNIV OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction mainly has two disadvantages: one is that the nitro substitution of the 3-position and the 5-position of salicylaldehyde is a competitive reaction, which leads to the content of the by-product 3-nitrosalicylaldehyde in the synthesized nitrosalicylaldehyde It is relatively high, which causes great difficulties for the separation and purification in the later stage; the second is that due to the intense heat release of the initial reaction, in order to control the reaction, it must be carried out in an ice-water bath, but the reaction rate at low temperature is small.
As a result, the yield is reduced, which is unfavorable for the large-scale production of 5-nitrosalicylaldehyde

Method used

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  • New preparation method of 5-nitro-salicylaldehyde
  • New preparation method of 5-nitro-salicylaldehyde
  • New preparation method of 5-nitro-salicylaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Measure 100ml of glacial acetic acid, 12.5g of hydrofluoric acid, 25.9g of acetic anhydride, and 25.7g of salicylaldehyde into a 250ml three-neck flask in turn, and keep stirring in an ice-water bath to cool below 5°C. Put 16.6g of fuming nitric acid in a constant pressure dropping funnel, control the temperature within the range of 5-10°C, and evenly drop the fuming nitric acid into the three-necked flask within 2.5 hours. Then control the temperature at 8-10°C to react for 1 hour, then raise the temperature to 15-20°C to continue the reaction for 1 hour. While hot, pour the reaction solution into a mixture of 500 g of crushed ice and water, stir evenly, and let stand for 5 hours (or stand overnight). Suction filtration, washing and drying gave 28.3 g of yellow powder solid. After water extraction, 14.8 g of light yellow 5-nitrosalicylaldehyde powder was obtained with a yield of 52%.

[0023] Infrared spectrum (KBr, cm -1 ): 3069cm -1 ;2883cm -1 ;1664cm -1 ;1625,...

Embodiment 2

[0026] Measure 100ml of glacial acetic acid, 12.5g of hydrofluoric acid, 25.9g of acetic anhydride, and 25.7g of salicylaldehyde into a 250ml three-neck flask in turn, and keep stirring in an ice-water bath to cool below 5°C. Put 16.6g of fuming nitric acid in a constant pressure dropping funnel, control the temperature in the range of 5 to 102, and evenly drop the fuming nitric acid into the three-necked flask within 2.5 hours. Then control the temperature at 8-10°C to react for 1 hour, then raise the temperature to 15-20°C to continue the reaction for 1 hour. While hot, pour the reaction solution into 500g of crushed ice and water mixture, stir evenly, and let stand for 5h (or stand overnight). Suction filtration, washing and drying gave 25.5 g of yellow powder solid. After water extraction, 12.7 g of light yellow 5-nitrosalicylaldehyde powder was obtained with a yield of 50%.

[0027] Infrared spectrum (KBr, cm -1 ): 3070cm -1 ;2885cm -1 ;1657cm -1 ;1614, 1578, 1447cm...

Embodiment 3

[0030] Measure 100ml of glacial acetic acid, 5.0g of hydrofluoric acid, 25.9g of acetic anhydride, and 25.7g of salicylaldehyde into a 250ml three-neck flask in turn, and keep stirring in an ice-water bath to cool below 5°C. Put 16.6g of fuming nitric acid in a constant pressure dropping funnel, control the temperature within the range of 5-10°C, and evenly drop the fuming nitric acid into the three-necked flask within 2.5 hours. Then control the temperature at 8-10°C to react for 1 hour, then raise the temperature to 15-20°C to continue the reaction for 1 hour. While hot, pour the reaction solution into 500g of crushed ice and water mixture, stir evenly, and let stand for 5h (or stand overnight). Suction filtration, washing and drying gave 32.0 g of yellow powder solid. After water extraction, 12.6 g of light yellow 5-nitrosalicylaldehyde powder was obtained with a yield of 39%. The reason for the substantial reduction in the yield of this synthesis is that the amount of hy...

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Abstract

The invention belongs to the technical field of preparation of chemical intermediates needed by the synthetic process of medicine, dye, pesticide, spice and the like, and particularly relates to a method for preparing 5-nitro-salicylaldehyde by an improved low-temperature nitration method, which takes salicylaldehyde as a raw material; and the 5-nitro-salicylaldehyde is prepared by the improved low-temperature nitration method. In the reaction process, a brand new ternary mixed solvent system consisting of hydrofluoric acid, acetic anhydride and acetic acid is adopted, so that the reaction speed of low-temperature nitration and the yield of the 5-nitro-salicylaldehyde synthesized by the nitration method can be successfully improved. The synthesis conditions of the method can be easily controlled, so that the method is especially suitable for preparing the 5-nitro-salicylaldehyde in a laboratory; and meanwhile, the raw materials are easily obtained, and the production cost is comparatively low, so that the method has certain implementation value and socio-economic benefit.

Description

technical field [0001] The invention belongs to the technical field of preparation of chemical intermediates in the synthesis process of medicines, dyes, pesticides and spices, and specifically relates to an improved method for preparing 5-nitrosalicylaldehyde through low-temperature nitration. Background technique [0002] 5-Nitrosalicylaldehyde is a chemical intermediate widely used in the synthesis of medicines, dyes, pesticides and spices. In the development and utilization of drugs, Dronedarone hydrochloride synthesized from 5-nitrosalicylaldehyde has a chemical name of 2-n-butyl-3-[4-(3-di-n-butylamino Propoxy)benzoyl]-5-methanesulfonamidobenzofuran is an important drug for the treatment of cardiovascular diseases; in the synthesis of marine drug chitosan, the hydroxyl group prepared by 5-nitrosalicylaldehyde The antibacterial effect and antioxidant capacity of propyl chitosan Schiff base are significantly higher than those of hydroxypropyl chitosan Schiff base prepar...

Claims

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Application Information

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IPC IPC(8): C07C205/44C07C201/08
Inventor 田进涛田卫国
Owner OCEAN UNIV OF CHINA
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