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Method for efficiently and rapidly synthesizing o-amino benzaldehyde

A technology of o-aminobenzaldehyde and o-nitrotoluene, which is applied in chemical instruments and methods, preparation of organic compounds, organic compound/hydride/coordination complex catalysts, etc., can solve long reaction time, harsh reaction conditions, high cost

Active Publication Date: 2015-12-16
TAIZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the literature reports in recent years, Chinese and foreign scholars are relatively mature in the one-step synthesis of p-aminobenzaldehyde, and obtain a higher yield of more than 90%, but the one-step synthesis of o-aminobenzaldehyde is progressing slowly, and the literature reports only 8 % yield (document: Synthesis, 1978 (1), 23-4.), therefore the synthetic anthranilaldehyde of actual large-scale production all can be realized by multi-step reaction, therefore used excessive reagent, Long reaction time, harsh reaction conditions and the use of a large amount of solvent, and the yield is poor, which deviates from the concept of green chemistry, and the cost is quite high

Method used

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  • Method for efficiently and rapidly synthesizing o-amino benzaldehyde
  • Method for efficiently and rapidly synthesizing o-amino benzaldehyde
  • Method for efficiently and rapidly synthesizing o-amino benzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Place the sodium polysulfide solution (0.1mol) in a 100mL three-necked flask, add 50mL of anhydrous methanol and 5mmol of ionic liquid with stirring, heat to 50℃, slowly add o-aminotolualdehyde (0.1mol) dropwise, then reflux and stir After 2 hours, HPLC tracked detection. After the raw materials disappeared, the reaction solution was extracted with dichloromethane, the organic phases were combined, the organic solvent was removed under reduced pressure, and the product was obtained after vacuum drying. The yield was 87.1% and the content was 96.5% (HPLC detection).

Embodiment 2

[0026] Place the sodium polysulfide solution (0.1mol) in a 100mL three-necked flask, add 50mL of anhydrous methanol and 5mmol of ionic liquid with stirring, heat to 50℃, slowly add o-aminotolualdehyde (0.1mol) dropwise, then reflux and stir After 3 hours, HPLC tracking detection, the raw materials disappeared, the reaction solution was extracted with dichloromethane, the organic phases were combined, the organic solvent was removed under reduced pressure, and the product was obtained after vacuum drying. The yield was 90.2% and the content was 96.8% (HPLC detection).

Embodiment 3

[0028] Place the sodium polysulfide solution (0.1mol) in a 100mL three-necked flask, add 50mL of anhydrous methanol and 5mmol of ionic liquid with stirring, heat to 50℃, slowly add o-aminotolualdehyde (0.1mol) dropwise, then reflux and stir After 5 hours, HPLC tracking detection, the raw materials disappeared, the reaction solution was extracted with dichloromethane, the organic phases were combined, the organic solvent was removed under reduced pressure, and the product was obtained after vacuum drying. The yield was 92.6% and the content was 96.2% (HPLC detection).

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Abstract

The invention relates to a method for efficiently and rapidly synthesizing o-amino benzaldehyde from ortho-nitrotoluene under the mild reaction condition by using an environmental-friendly catalyst. The method comprises the step of synthesizing the o-amino benzaldehyde from the ortho-nitrotoluene by taking functionalized ionic liquid as the catalyst and alcohol as solvent under the normal pressure condition and the existence of sodium polysulfide; the ionic liquid has a remarkable catalytic effect; the method is simple in operation and high in yield, and has mild conditions of a catalytic reaction system and a broad industrial application prospect.

Description

Technical field [0001] The invention relates to a method for synthesizing o-aminobenzaldehyde in one step from o-nitrotoluene under high-efficiency, green and mild reaction conditions, using a novel functional ionic liquid as a catalyst. technical background [0002] O-aminobenzaldehyde is an important intermediate and is widely used in fine chemical and pharmaceutical fields. In medicine, it can further synthesize 2-amino-3,5-dibromobenzaldehyde, and it is a very important intermediate for the synthesis of ambroxol. Ambroxol was first developed and marketed by the German company Boehringer Ingelheim in 1984, and has now become a good new expectorant drug approved for use in many countries in the world, and its use in current drugs is considerable. One-step synthesis of o-aminobenzaldehyde from o-nitrotoluene, exploring the green synthesis of pharmaceutical intermediates, and reducing product costs have become a hot topic for researchers. According to literature reports in rece...

Claims

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Application Information

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IPC IPC(8): C07C223/06C07C221/00C07D487/04B01J31/04
Inventor 邱方利应安国莫寒劼李嵘嵘
Owner TAIZHOU UNIV
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