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3-methoxy-4-aminobenzoic acid and preparing method thereof

A technology of aminobenzoic acid and nitrobenzoic acid, applied in the field of biomedicine, can solve problems such as difference, and achieve the effects of high purity, few by-products and high yield

Inactive Publication Date: 2016-06-29
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for 3-methoxy-4-aminobenzoic acid, due to the structural difference between the two, the operating reaction conditions and catalyst selection that need to be paid attention to in the specific preparation process will be very different.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve 1mol of 3-hydroxy-4-nitrobenzoic acid in 17L of absolute ethanol and add it to the reaction kettle, then add 20g of NaOH to it, stir to dissolve it, then add 1.5mol of methyl bromide to it dropwise, control the temperature at 40°C, and continue After reacting for 2 hours, add dilute hydrochloric acid to adjust the pH to 5, add saturated saline, and precipitate crystals, namely 3-methoxy-4-nitrobenzoic acid; dissolve the prepared 3-methoxy-4-nitrobenzoic acid in Add 7g of carbon nanoparticles to 15L of anhydrous THF, and feed hydrogen gas at a rate of 60mL / min, adjust the pressure to 0.5MPa, and control the temperature at 120°C. After continuing the reaction for 2 hours, lower the temperature, filter, and evaporate THF Yellow crystals were obtained, which were recrystallized with a mixture of petroleum ether / ethyl acetate with a mass fraction of 5:1 to obtain pure 3-methoxy-4-aminobenzoic acid.

[0021] The purity of the obtained product was 80.2%, and the yield...

Embodiment 2

[0023] Dissolve 1mol of 3-hydroxy-4-nitrobenzoic acid in 18L of absolute ethanol and add it to the reaction kettle, then add 16.2g of NaOH to it, stir to dissolve it, then add 1.6mol of methyl bromide dropwise to it, and control the temperature at 45°C. After continuing the reaction for 2 hours, add dilute hydrochloric acid to adjust the pH to 6, add saturated saline, and precipitate crystals, namely 3-methoxy-4-nitrobenzoic acid; dissolve the prepared 3-methoxy-4-nitrobenzoic acid In 17L of anhydrous THF, add 5g of carbon nanoparticles, and pass hydrogen gas at a rate of 65mL / min, adjust the pressure to 1MPa, and control the temperature at 120°C. After continuing the reaction for 2h, lower the temperature, filter, and evaporate THF Yellow crystals were obtained, which were recrystallized with a mixture of petroleum ether / ethyl acetate with a mass fraction of 5:1 to obtain pure 3-methoxy-4-aminobenzoic acid.

[0024] The purity of the obtained product was 82.3%, and the yield ...

Embodiment 3

[0026] Dissolve 1mol of 3-hydroxy-4-nitrobenzoic acid in 20L of absolute ethanol and add it to the reaction kettle, then add 16g of NaOH to it, stir to dissolve it, then add 1.7mol of methyl bromide dropwise to it, control the temperature at 55°C, and continue After reacting for 2 hours, add dilute hydrochloric acid to adjust the pH to 6, add saturated saline, and precipitate crystals, namely 3-methoxy-4-nitrobenzoic acid; dissolve the prepared 3-methoxy-4-nitrobenzoic acid in Add 6.5g of carbon nanoparticles to 16L of anhydrous THF, and pass hydrogen gas at a rate of 70mL / min, adjust the pressure to 0.2MPa, and control the temperature at 120°C. After continuing the reaction for 2 hours, lower the temperature, filter, and evaporate THF gave yellow crystals, which were recrystallized with a mixture of petroleum ether / ethyl acetate with a mass fraction of 5:1 to obtain pure 3-methoxy-4-aminobenzoic acid.

[0027] The purity of the obtained product was 86.8%, and the yield was 92...

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PUM

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Abstract

The invention aims at providing a 3-methoxy-4-aminobenzoic acid and a preparing method thereof. The preparing method includes the steps that 3-hydroxy-4-nitrobenzoic acid serves as a raw material and is reacted with bromomethane to generate 3-methoxy-4-nitrobenzoic acid, active carbon serves as a reducing agent, the pressure and the temperature are controlled, and the 3-methoxy-4-aminobenzoic acid is prepared. According to the preparing method, the suitable catalyst is used, the reaction temperature and the reaction pressure are controlled, the purity and the yield of the product are increased, and the whole procedure is low in cost, convenient to operate and suitable for large-scale industrial production.

Description

Technical field: [0001] The invention relates to the technical field of biomedicine, in particular to 3-methoxy-4-aminobenzoic acid and a preparation method thereof. Background technique: [0002] p-Aminobenzoic acid is an important intermediate in organic synthesis, and plays a more prominent role in pharmaceutical synthesis due to its unique biological activity. It is an important intermediate in the synthesis of the non-steroidal anti-inflammatory drug felbinac, which is safe and effective in the treatment of joint diseases and muscle pain. In addition, derivatives of p-aminobenzoic acid are also widely used anesthetics, which can relieve symptoms such as anemia and diarrhea. At the same time, derivatives of p-aminobenzoic acid can also be used to treat diseases such as rickets, arthritis, rheumatism and tuberculosis. The 3-methoxy substituted p-aminobenzoic acid also plays a very important role in pharmaceutical synthesis. [0003] Domestic patent documents introduce ...

Claims

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Application Information

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IPC IPC(8): C07C227/04C07C229/64C07C201/12C07C205/59
CPCC07C227/04C07C201/12C07C229/64C07C205/59
Inventor 叶芳
Owner 叶芳