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A kind of efficient, fast method for synthesizing o-aminobenzaldehyde

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 slow progress, long reaction time, yield, etc. Rate difference and other issues

Active Publication Date: 2018-02-02
TAIZHOU UNIV +1
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  • Abstract
  • Description
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  • Application Information

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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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  • A kind of efficient, fast method for synthesizing o-aminobenzaldehyde
  • A kind of efficient, fast method for synthesizing o-aminobenzaldehyde
  • A kind of efficient, fast method for synthesizing o-aminobenzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Put sodium polysulfide solution (0.1mol) in a 100mL three-neck flask, add 50mL of anhydrous methanol and 5mmol ionic liquid under stirring, heat to 50°C, slowly add o-aminotolualdehyde (0.1mol) dropwise, and then reflux and stir After 2 hours, HPLC followed 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] Put sodium polysulfide solution (0.1mol) in a 100mL three-neck flask, add 50mL of anhydrous methanol and 5mmol ionic liquid under stirring, heat to 50°C, slowly add o-aminotolualdehyde (0.1mol) dropwise, and then reflux and stir After 3 hours, HPLC traced and detected that 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 with a yield of 90.2% and a content of 96.8% (detected by HPLC).

Embodiment 3

[0028] Put sodium polysulfide solution (0.1mol) in a 100mL three-neck flask, add 50mL of anhydrous methanol and 5mmol ionic liquid under stirring, heat to 50°C, slowly add o-aminotolualdehyde (0.1mol) dropwise, and then reflux and stir After 5 hours, HPLC tracking detection showed that 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 with a yield of 92.6% and a content of 96.2% (HPLC detection).

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Abstract

The invention relates to a method for efficiently and rapidly synthesizing anthranilaldehyde from o-nitrotoluene in one step using an environmentally friendly catalyst under mild reaction conditions. In the presence of sodium polysulfide, anthranilaldehyde can be synthesized from o-nitrotoluene in one step using alcohol as a solvent. The catalytic effect of ionic liquid is remarkable.

Description

technical field [0001] The invention relates to a method for synthesizing o-aminobenzaldehyde from o-nitrotoluene in one step by using a novel functional ionic liquid as a catalyst under high-efficiency, green, and mild reaction conditions. technical background [0002] Anthranilaldehyde 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, which is a very important intermediate for the synthesis of ambroxol. Ambroxol was first developed and listed by German Boehringer Ingelheim Company in 1984, and has now become a good expectorant new drug approved by many countries in the world, and its usage in current medicines is quite considerable. One-step synthesis of o-aminobenzaldehyde from o-nitrotoluene, exploration of green synthesis of pharmaceutical intermediates, and reduction of product costs have become a hot topic for researchers. According to the literature rep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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