O-nitrotoluene aldehyde synthesis method

A technology of nitrotolualdehyde and o-nitrobenzaldehyde, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of harsh reaction conditions, long reaction time, poor yield, etc. high rate effect

Inactive Publication Date: 2017-12-19
ZHANGJIAGANG JINFENG RUNERFA HARDWARE PLASTIC FACTORY
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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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 1. Combine o-nitrotolualdehyde and FeSO 4 ·7H 2 O and the aqueous solution are fully stirred and mixed;

[0020] 2. Add concentrated hydrochloric acid dropwise for 10 minutes, continue to stir and raise the temperature to 90°C;

[0021] 3. Add ammonia water dropwise, continue to stir and react at 90°C for 20 minutes, and track the progress of the reaction with high performance liquid chromatography (HPLC);

[0022] 4. Carry out steam distillation on the reaction solution to obtain fractions, add the fractions into cooled saturated brine, and precipitate crystals.

[0023] Its melting point is 35-36°C measured with a melting point apparatus.

[0024] In this embodiment, o-nitrotolualdehyde and FeSO 4 ·7H 2 The molar ratio of O is 1:17; the molar ratio of aqueous solution to ammonia water is: 3:1.

[0025] Yield 91%, content 95% (HPLC detection).

Embodiment 2

[0027] 1. Combine o-nitrotolualdehyde and FeSO 4 ·7H 2 O and the aqueous solution are fully stirred and mixed;

[0028] 2. Add concentrated hydrochloric acid dropwise for 15 minutes, continue to stir and raise the temperature to 90°C;

[0029] 3. Add ammonia water dropwise, continue to stir and react for 30 minutes at a temperature of 90°C, and track the progress of the reaction with high performance liquid chromatography (HPLC);

[0030] 4. Carry out steam distillation on the reaction solution to obtain fractions, add the fractions into cooled saturated brine, and precipitate crystals.

[0031] Its melting point is 35-36°C measured with a melting point apparatus.

[0032] In this embodiment, o-nitrotolualdehyde and FeSO 4 ·7H 2 The molar ratio of O is 1:15; the molar ratio of aqueous solution to ammonia water is 2:1.

[0033] Yield 90.5%, content 94% (HPLC detection).

Embodiment 3

[0035] 1. Combine o-nitrotolualdehyde and FeSO 4 ·7H 2 O and the aqueous solution are fully stirred and mixed;

[0036] 2. Add concentrated hydrochloric acid dropwise for 12 minutes, continue to stir and raise the temperature to 80°C;

[0037] 3. Add ammonia water dropwise, continue to stir and react at 80°C for 20 minutes, and track the progress of the reaction with high performance liquid chromatography (HPLC);

[0038] 4. Carry out steam distillation on the reaction solution to obtain fractions, add the fractions into cooled saturated brine, and precipitate crystals.

[0039] Its melting point is 35-36°C measured with a melting point apparatus.

[0040] In this embodiment, o-nitrotolualdehyde and FeSO 4 ·7H 2 The molar ratio of O is 1:20; the molar ratio of aqueous solution to ammonia water is 2.6:1.

[0041] Yield 89%, content 93% (HPLC detection).

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Abstract

The present application discloses an o-nitrotoluene aldehyde synthesis method, wherein o-nitrobenzaldehyde is subjected to a reducing reaction by using o-nitrobenzaldehyde as a starting raw material and using FeSO4.7H2O as a reducing agent to prepare o-aminobenzaldehyde. According to the present invention, the o-aminobenzaldehyde is synthesized by using FeSO4.7H2O as the reducing agent, such that the yield is high, and the method is pollution-free.

Description

technical field [0001] The application relates to a synthetic method of o-nitrotolualdehyde. Background technique [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 BoehringerIngelheim 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 reports in recent years, Chinese and foreign scholars are relatively mature in the one-step synthesis of p-aminobenzaldehyde, and obtain a higher yield ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C223/06
CPCC07C221/00C07C223/06
Inventor 沈玉忠
Owner ZHANGJIAGANG JINFENG RUNERFA HARDWARE PLASTIC FACTORY
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