IES86998B2 - Drugs intermediates m-amionbenzoic acid synthesis method - Google Patents
Drugs intermediates m-amionbenzoic acid synthesis method Download PDFInfo
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- IES86998B2 IES86998B2 IES20180098A IES20180098A IES86998B2 IE S86998 B2 IES86998 B2 IE S86998B2 IE S20180098 A IES20180098 A IE S20180098A IE S20180098 A IES20180098 A IE S20180098A IE S86998 B2 IES86998 B2 IE S86998B2
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Abstract
Drugs intermediates m-aminobenzoic acid synthesis method, comprises the following steps: adding 3 mol cuprous chloride, 4-5 mol toluene and 5 mol m-nitrobenzoic acid to the reaction vessel, raising the temperature of the solution to 60 to 70°C, controlling the stirring speed to 110 to 130 rpm, kept for 90-110 min, adjust the solution pH to 9--10 with sodium hydroxide solution, reduce the solution temperature to 5-10°C, crystals precipitated, washed with 6L ethanol solution, washed with sodium chloride solution, and washed with nitromethane solution, and washed with diamine solution, and dehydrated with the dehydrating agent to obtain the m-aminobenzoic acid product.
Description
The present invention relates to drugs intermediates m-aminobenzoic acid .
synthesis method.
GENERAL BACKGROUND
Aminobenzoic acid is mainly used in the synthesis of pharmaceutical intermediates, however, in most or the existing synthetic methods, iron powder is used 10 as reactant and it is very complicated, the final yield is not very high. Therefore, it is necessary to propose a new synthetic method for further improving the quality and yield of the product and reducing the byproduct content, it has important economic significance.
SUMMARY
The purpose of the present invention is to provide drugs intermediates m-aminobenzoic acid synthesis method, comprises the following steps:
(i) adding 3 mol cuprous chloride, 4-5 mol toluene and 5 mol m-nitrobenzoic acid to the reaction vessel, raising the temperature of the solution to 60 to 70 °C, controlling 20 the stirring speed to 110 to 130 rpm, kept for 90-110 min, adjust the solution pH to
9— 10 with sodium hydroxide solution, reduce the solution temperature to 5-10°C, crystals precipitated, washed with 6L ethanol solution, washed with sodium chloride solution, and washed with nitromethane solution, and washed with ethylene diamine solution, and dehydrated with the dehydrating agent to obtain the m-aminobenzoic acid product; wherein, the mass fraction of the sodium hydroxide solution in the step (i) is
- 15%, the mass fraction of the ethanol solution in the step (i) is 30-35%, the mass fraction of the sodium chloride solution in the step (i) is 40-45%, the mass of the nitromethane solution in the step (i) 50-56%, the mass fraction of the ethylene diamine solution in step (i) is 60-65%, and the dehydrating agent in the step (i) is any one of anhydrous sodium sulfate and anhydrous magnesium sulfate.
Throughout the reaction process can be the following reaction formula:
Advantage of the present invention is that: reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
drugs intermediates m-aminobenzoic acid synthesis method.
08/02/2019
Embodiment 1 mol cuprous chloride, 4 mol toluene and 5 mol m-nitrobenzoic acid solution were added to the reaction vessel, the temperature of the solution was increased to 60 °C, the stirring speed was controlled to 110 rpm and kept for 90 min, using the sodium hydroxide solution with a mass fraction of 10% to adjust the solution pH to 9, reducing the solution temperature to 50°C, the crystal precipitated, washed with 6L ethanol solution with a mass fraction of 30%, washed with sodium chloride solution with a mass fraction of 40%, and washed with nitromethane solution with a mass fraction of 50%, and with 60% ethylene diamine solution and dehydrated with anhydrous sodium sulfate dehydrating agent to obtain the m-aminobenzoic acid product 357.57 g , yield 87%.
Embodiment 2 mol cuprous chloride, 4.5 mol toluene and 5 mol m-nitrobenzoic acid were added to the reaction vessel, the temperature of the solution was raised to 65 °C and the stirring speed was kept at 120 rpm for 100 min, using the sodium hydroxide solution with a mass fraction of 12 % to adjust the solution to pH 9.5, reducing the solution
08/02/2019 temperature to 7°C, the crystal precipitated, washed with 6L ethanol solution with a mass fraction of 32%, and with sodium chloride solution with a mass fraction of 42%, washed with nitromethane solution with a mass fraction of 53%, washed with ethylene diamine solution with a mass fraction of 63%, dehydrated wth anhydrous magnesium 5 sulfate dehydrating agent to obtain the m-aminobenzoic acid product 374.0lg, yield 91%.
Embodiment 3 mol cuprous chloride, 5 mol toluene and 5 mol m-nitrobenzoic acid were added to the reaction vessel, the temperature of the solution was raised to 70°C and the stirring speed was controlled at 130 rpm for 110 min, using the sodium hydroxide solution with a mass fraction 15 % to adjust the solution to pH 10, reducing the solution temperature to 10 °C, the crystal precipitated, washed with 6L ethanol solution with a mass fraction of 35%, washed with sodium chloride solution with a mass fraction of 45%, washed with nitromethane solution with a mass fraction of 56%, and with the ethylene diamine solution with a the mass fraction of 65%, dehydrated with anhydrous sodium sulfate dehydrating agent to obtain the m-aminobenzoie acid product 382.23g, yield 93%.
Claims (3)
1. Drugs intermediates m-aminobenzoic acid synthesis method, comprises the following steps: (i) adding 3 mol cuprous chloride, 4-5 mol toluene and 5 mol m-nitrobenzoic 5 acid to the reaction vessel, raising the temperature of the solution to 60 to 70°C, controlling the stirring speed to 110 to 130 rpm, kept for 90-110 min, adjust the solution pH to 9—10 with sodium hydroxide solution, reduce the solution temperature to 5-10°C, crystals precipitated, washed with 6L ethanol solution, washed with sodium chloride solution, and washed with nitromethane solution, and washed with ethylene 10 diamine solution, and dehydrated with the dehydrating agent to obtain the m-aminobenzoic acid product; wherein, the mass fraction of the sodium hydroxide solution in the step (i) is 10-15%, the mass fraction of the ethanol solution in the step (i) is 30-35%, the mass fraction of the sodium chloride solution in the step (i) is 40-45%, the mass of the nitromethane solution in the step (i) 50-56%.
2. Drugs intermediates m-aminobenzoic acid synthesis method according to claim 1 wherein the mass fraction of the ethylene diamine solution in step (i) is 60-65%. 20
3. Drugs intermediates m-aminobenzoic acid synthesis method according to claim 1 wherein the dehydrating agent in the step (i) is any one of anhydrous sodium sulfate and anhydrous magnesium sulfate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180098A IES86998B2 (en) | 2018-04-03 | 2018-04-03 | Drugs intermediates m-amionbenzoic acid synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180098A IES86998B2 (en) | 2018-04-03 | 2018-04-03 | Drugs intermediates m-amionbenzoic acid synthesis method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IES20180098A2 IES20180098A2 (en) | 2019-05-01 |
| IES86998B2 true IES86998B2 (en) | 2019-05-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IES20180098A IES86998B2 (en) | 2018-04-03 | 2018-04-03 | Drugs intermediates m-amionbenzoic acid synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IES86998B2 (en) |
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2018
- 2018-04-03 IE IES20180098A patent/IES86998B2/en unknown
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| IES20180098A2 (en) | 2019-05-01 |
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