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Procaine hydrochloride drug intermediate p-nitrobenzoic acid synthesis method

A technology of procaine hydrochloride and p-nitrobenzoic acid, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of low safety factor in the production process, large environmental pollution, complex production process and the like , to achieve the effect of shortening the reaction time, increasing the reaction yield, and improving the reaction yield

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

This generation method needs to use a large amount of sodium dichromate, manganese ore powder, nitric acid, sulfuric acid, etc. as raw materials for reaction and generation. The safety factor is low, and the production process is relatively complicated, so it is necessary to propose a new synthetic method

Method used

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  • Procaine hydrochloride drug intermediate p-nitrobenzoic acid synthesis method
  • Procaine hydrochloride drug intermediate p-nitrobenzoic acid synthesis method
  • Procaine hydrochloride drug intermediate p-nitrobenzoic acid synthesis method

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Experimental program
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Effect test

Embodiment 1

[0017] The synthetic method of procaine hydrochloride pharmaceutical intermediate p-nitrobenzoic acid comprises the steps:

[0018] A. Add 3mol of 4-nitro-6-hydroxybenzyl alcohol into the reaction vessel, raise the temperature of the solution to 46°C, control the stirring speed at 110rpm, and add 4mol of 3-methyl-2-butanone with a mass fraction of 80%. Solution, 2mol of samarium oxide powder, raise the temperature of the solution to 60°C;

[0019] B. Continue to react for 90 minutes, lower the solution temperature to 10°C, filter, wash 3 times with 30% potassium sulfate solution, 5 times with 10% oxalic acid solution, and 80% 2-chloro- Wash 6 times with 2-methylpropane solution, recrystallize in thiodiglycol solution with a mass fraction of 90%, and dehydrate with anhydrous calcium sulfate dehydrating agent to obtain 455.91 g of p-nitrobenzoic acid with a mass fraction of 91%.

Embodiment 2

[0021] The synthetic method of procaine hydrochloride pharmaceutical intermediate p-nitrobenzoic acid comprises the steps:

[0022] A. Add 3mol of 4-nitro-6-hydroxybenzyl alcohol to the reaction vessel, increase the solution temperature to 49°C, control the stirring speed at 120rpm, and add 4.5mol of 3-methyl-2-butanol with a mass fraction of 83%. Ketone solution, 2.5mol samarium oxide powder, raise the solution temperature to 63°C;

[0023] B. Continue to react for 110 minutes, lower the solution temperature to 15°C, filter, wash 4 times with 35% potassium sulfate solution, 6 times with 13% oxalic acid solution, and 82% 2-chloro-2 -Methyl propane solution washed 7 times, recrystallized in thiodiglycol solution with a mass fraction of 93%, and dehydrated with anhydrous potassium carbonate dehydrating agent to obtain 465.93 g of p-nitrobenzoic acid with a yield of 93%.

Embodiment 3

[0025] The synthetic method of procaine hydrochloride pharmaceutical intermediate p-nitrobenzoic acid comprises the steps:

[0026] A. Add 3mol of 4-nitro-6-hydroxybenzyl alcohol into the reaction vessel, raise the temperature of the solution to 55°C, control the stirring speed at 130rpm, and add 5mol of 3-methyl-2-butanol with a mass fraction of 86%. Ketone solution, 3mol samarium oxide powder, raise the solution temperature to 69°C;

[0027] B. Continue to react for 130min, lower the solution temperature to 18°C, filter, wash 5 times with 40% potassium sulfate solution, 6 times with 17% oxalic acid solution, and 85% 2-chloro - Washing 7 times with 2-methylpropane solution, recrystallizing in 96% thiodiglycol solution, and dehydrating with anhydrous calcium sulfate dehydrating agent to obtain 480.96 g of p-nitrobenzoic acid with a yield of 96%.

[0028] Finished product p-nitrobenzoic acid is done infrared analysis, gets infrared analysis spectrogram, as figure 1 shown. Th...

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Abstract

The invention discloses a procaine hydrochloride drug intermediate p-nitrobenzoic acid synthesis method, which comprises: adding 4-nitro-6-hydroxybenzyl alcohol in a reaction container, increasing thetemperature of the solution, controlling the stirring, adding a 3-methyl-2-butanone solution and samarium oxide powder, increasing the temperature of the solution, continuously carrying out the reaction, reducing the temperature of the solution, filtering, washing multiple times with a potassium sulfate solution, washing multiple times with an oxalic acid solution, washing multiple times with a 2-chloro-2-methylpropane solution, re-crystallizing in a thiodiglycol solution, and dehydrating with a dehydrating agent to obtain the finished product p-nitrobenzoic acid.

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 p-nitrobenzoic acid, a procaine hydrochloride pharmaceutical intermediate. Background technique [0002] p-Nitrobenzoic acid is an intermediate in organic synthesis of medicines, dyes, veterinary drugs, and photosensitive materials. Used in the production of procaine hydrochloride, procainamide hydrochloride, p-aminomethylbenzoic acid, folic acid, benzocaine, cough, cephalosporin V, p-aminobenzoyl glutamic acid, shellfish Nier, and the production of reactive brilliant red M-8B, reactive red violet X-2R and filters, color film couplers, metal surface rust removers, sunscreens, etc. Procaine hydrochloride acts on peripheral nerves to produce a conduction block effect, relying on a concentration gradient to penetrate the nerve cell membrane in a diffuse manner, blocking sodium ion channels on ...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/57
CPCC07C201/12C07C205/57
Inventor 彭飞
Owner CHENGDU QIESITE TECH CO LTD
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