Nifedipine drug intermediate o-nitrobenzaldehyde synthesis method

A technology of nitrobenzaldehyde and nifedipine, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of complicated process and low final yield, and achieve improved reaction yield and reaction time The effect of shortening and reducing the intermediate links of the reaction

Inactive Publication Date: 2018-07-03
CHENGDU QIESITE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the existing synthetic methods are obtained by nitration and oxidation of o-nitrotoluene. The process is relatively complicated and the final yield is not high. Therefore, it is necessary to propose a new synthetic method

Method used

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  • Nifedipine drug intermediate o-nitrobenzaldehyde synthesis method
  • Nifedipine drug intermediate o-nitrobenzaldehyde synthesis method
  • Nifedipine drug intermediate o-nitrobenzaldehyde synthesis method

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Experimental program
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Effect test

Embodiment 1

[0018] The synthetic method of nifedipine medicine intermediate o-nitrobenzaldehyde comprises the steps:

[0019] A, 2mol of 3-bromo-2-(1-hydroxyethyl)-nitrobenzene and 700ml mass fraction of 15% sodium nitrate solution are added to the reaction vessel, the stirring speed is controlled to 110rpm, and the temperature of the solution is lowered to 10°C. Reaction 60min, the mass fraction that adds 3mol is the dichlorobutene solution of 40%, adds 2mol rhodium trichloride in 3 times;

[0020] B. Continue to react for 40 minutes, separate layers, extract 3 times with 50% chlorodibromomethane solution, 5 times with 60% thionyl chloride solution, wash with 20% potassium nitrate solution Three times, the oil layer was separated, dehydrated with an activated alumina dehydrating agent, and recrystallized in a 3-chlorobenzotrifluoride solution with a mass fraction of 85%, to obtain 274.82 g of finished product o-nitrobenzaldehyde, with a yield of 91%.

Embodiment 2

[0022] The synthetic method of nifedipine medicine intermediate o-nitrobenzaldehyde comprises the steps:

[0023] A. Add 2mol of 3-bromo-2-(1-hydroxyethyl)-nitrobenzene and 750ml mass fraction of 18% sodium nitrate solution into the reaction vessel, control the stirring speed to 120rpm, reduce the solution temperature to 13°C, and react 70min, adding 3.5mol mass fraction is 43% dichlorobutene solution, adding 2.5mol rhodium trichloride in 4 times;

[0024] B. Continue to react for 50 minutes, separate the layers, extract 4 times with a 53% chlorodibromomethane solution, extract 6 times with a 64% thionyl chloride solution, and wash with a 23% potassium nitrate solution 5 times, the oil layer was separated, dehydrated with anhydrous calcium chloride dehydrating agent, and recrystallized in 3-chlorobenzotrifluoride solution with a mass fraction of 88%, to obtain 280.86 g of finished product o-nitrobenzaldehyde, with a yield of 93%.

Embodiment 3

[0026] The synthetic method of nifedipine medicine intermediate o-nitrobenzaldehyde comprises the steps:

[0027] A. Add 2mol of 3-bromo-2-(1-hydroxyethyl)-nitrobenzene and 800ml mass fraction of 22% sodium nitrate solution into the reaction vessel, control the stirring speed to 130rpm, reduce the solution temperature to 15°C, and react 80min, add 4mol mass fraction and be 47% dichlorobutene solution, add 3mol rhodium trichloride in 6 times;

[0028] B, continue to react for 60min, the solution is layered, and the mass fraction is 56% chlorodibromomethane solution extraction 5 times, the mass fraction is 68% thionyl chloride solution extraction 7 times, and the mass fraction is 27% potassium nitrate solution After washing 6 times, the oil layer was separated, dehydrated with activated alumina dehydrating agent, and recrystallized in 92% 3-chlorobenzotrifluoride solution to obtain 289.92 g of finished product o-nitrobenzaldehyde, with a yield of 96%.

[0029] The finished prod...

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Abstract

The invention discloses a nifedipine drug intermediate o-nitrobenzaldehyde synthesis method, which comprises: adding 3-bromo-2-(1-hydroxyethyl)-nitrobenzene and a sodium nitrate solution to a reactioncontainer, controlling the stirring speed, reducing the temperature of the solution, carrying out a reaction for 60-80 min, adding a dichlorobutene solution, adding rhodium trichloride in batches, continuously carrying out the reaction, layering the solution, extracting multiple times with a chlorodibromomethane solution, extracting multiple times with a thionyl chloride solution, washing multiple times with a potassium nitrate solution, separating to obtain the oil layer, dehydrating with a dehydrating agent, and re-crystallizing in a 3-chlorobenzotrifluoride solution to obtain the finishedproduct o-nitrobenzaldehyde.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, belonging to the field of organic synthesis, in particular to a synthesis method of a nifedipine pharmaceutical intermediate o-nitrobenzaldehyde. Background technique [0002] O-nitrobenzaldehyde is used as a pharmaceutical intermediate, mainly used in the production of the drug nifedipine. Nifedipine is used to prevent and treat angina pectoris of coronary heart disease, especially variant angina pectoris and angina pectoris caused by coronary artery spasm. It has no adverse effect on respiratory function, so it is suitable for patients with angina pectoris with obstructive airway diseases, and its curative effect is better than that of beta-receptor antagonists. It is also suitable for various types of hypertension, and has a good effect on intractable and severe hypertension. Because it can reduce afterload, it also has good curative effect on refractory congestive hea...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/44
CPCC07C201/12C07C205/44
Inventor 彭飞
Owner CHENGDU QIESITE TECH CO LTD
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