AU2018100390A4 - Drugs intermediates o-aminobenzoic acid synthesis method - Google Patents
Drugs intermediates o-aminobenzoic acid synthesis method Download PDFInfo
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- AU2018100390A4 AU2018100390A4 AU2018100390A AU2018100390A AU2018100390A4 AU 2018100390 A4 AU2018100390 A4 AU 2018100390A4 AU 2018100390 A AU2018100390 A AU 2018100390A AU 2018100390 A AU2018100390 A AU 2018100390A AU 2018100390 A4 AU2018100390 A4 AU 2018100390A4
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- solution
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- aminobenzoic acid
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N NC(c1ccccc1)=O Chemical compound NC(c1ccccc1)=O KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Abstract Drugs intermediates o-aminobenzoic acid synthesis method, comprises the following steps: adding 3 mol benzamide in the reaction vessel, reducing the 5 temperature of the solution to 5-10 'C, controlling the stirring speed at 110-130 rpm, adding 4-5 mol 2-methyl phenol, 6 mol oxalic acid solution, the temperature was increased to 20-25 C for 90-130 min, 30g aluminum trichloride powder was added, the solution temperature was increased to 50-55"C, reacted for 30-40 min, 2 L sodium chloride solution was added, the temperature was lowered to 10-15 C, precipitated 10 white crystals, filter it, washed with cyclohexane solution, washed with isopropyl alcohol solution, dehydrated with dehydrating agent, drying at 60-65"C, finally got o-aminobenzoic acid product anthranilic acid.
Description
FIELD OF THE INVENTION
The present invention relates to drugs intermediates o-aminobenzoic acid 5 synthesis method.
GENERAL BACKGROUND
O-aminobenzoic acid is mainly used for the manufacture of dyes, drugs and spices, most of the existing synthetic methods using o-nitrotoluene as reactants, it is complicated and 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 o-aminobenzoic acid synthesis method, comprises the following steps:
(i) adding 3 mol benzamide in the reaction vessel, reducing the temperature of the solution to 5-10 °C, controlling the stirring speed at 110-130 rpm, adding 4-5 mol 2-methyl phenol, 6 mol oxalic acid solution, the temperature was increased to 20-25 °C for 90-130 min, 30g aluminum trichloride powder was added, the solution temperature was increased to 50-55°C, reacted for 30-40 min, 2 L sodium chloride solution was added, the temperature was lowered to 10-15°C, precipitated white crystals, filter it, washed with cyclohexane solution, washed with isopropyl alcohol solution, dehydrated with dehydrating agent, drying at 60-65°C, finally got o-aminobenzoic acid product anthranilic acid; wherein, the mass fraction of the sodium chloride solution in step (i) is 10-16%, the mass fraction of the cyclohexane solution in the step (i) is 30-40%, and the mass fraction of isopropyl alcohol solution in step (i) is 60- 65%, and the dehydrating agent in the step (i) is any one of anhydrous calcium chloride and anhydrous magnesium sulfate.
2018100390 28 Mar 2018
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 o-aminobenzoic acid synthesis method.
Embodiment 1
3mol benzamide was added into the reaction vessel, the temperature of the solution was reduced to 5°C, the stirring speed was controlled to 110 rpm, 4mol 2-methylphenol was added, 6mol oxalic acid solution with a mass fraction of 30% was added, the temperature was increased to 20 °C for 90 min, 30g aluminum trichloride powder was added, the reaction temperature was raised to 50 °C for 30 min, and 2 L sodium chloride solution with a mass fraction of 10% was added to reduce the temperature to 10 °C, and white crystals precipitated, fdter it, washed with cyclohexane solution with a mass fraction of 30%, and washed with isopropyl alcohol solution with a mass fraction of 60%, dehydrated with anhydrous calcium chloride dehydrating agent, drying at 60°C, finally got o-aminobenzoic acid product anthranilic acid 357.57 g, yield 87%.
2018100390 28 Mar 2018
Embodiment 2
3mol benzamide was added into the reaction vessel, the temperature of the solution was reduced to 7°C, the stirring speed was controlled at 120 rpm, 4.5mol 2-methylphenol was added, 6mol oxalic acid solution with a mass fraction of 33% was added, the temperature was increased to 23 °C for 120 min, 30g aluminum trichloride powder was added, the reaction temperature was raised to 52 °C, reacted for 35 min, 2 L sodium chloride solution with a mass fraction of 13%was added, the temperature was decreased to 12 °C, precipitated white crystals, filter it, washed with cyclohexane solution with a mass fraction of 35%, washed with isopropyl alcohol solution with a mass fraction of 63%, dehydrated with anhydrous magnesium sulfate dehydration, drying at 63°C, finally got o-aminobenzoic acid product anthranilic acid 374.0lg, yield 91%.
Embodiment 3
3 mol benzamide was added into the reaction vessel, the temperature of the solution was reduced to 10°C, the stirring speed was controlled at 130 rpm, 5 mol 2-methylphenol was added, 6 mol oxalic acid solution with a mass fraction of 37% was added, the temperature was increased to 25 °C for 130 min, 30g aluminum trichloride powder was added, the reaction temperature was raised to 55 °C, reacted for 40 min,
2L sodium chloride solution with a mass fraction of 16% was added, the temperature was lowered to 15 °C, white crystals precipitated, filter it, washed with cyclohexane solution with a mass fraction of 40%, washed with isopropyl alcohol solution with a mass fraction of 65%, dehydrated with anhydrous calcium chloride dehydrating agent, drying at 65 °C, finally got o-aminobenzoic acid product anthranilic acid 382.23g, yield of 93%.
2018100390 28 Mar 2018
Claims (3)
- Claims1. Drugs intermediates o-aminobenzoic acid synthesis method, comprises the following steps:(i) adding 3 mol benzamide in the reaction vessel, reducing the temperature of 5 the solution to 5-10 °C, controlling the stirring speed at 110-130 rpm, adding 4-5 mol
- 2-methyl phenol, 6 mol oxalic acid solution, the temperature was increased to 20-25 °C for 90-130 min, 30g aluminum trichloride powder was added, the solution temperature was increased to 50-55°C, reacted for 30-40 min, 2 L sodium chloride solution was added, the temperature was lowered to 10-15°C, precipitated white10 crystals, filter it, washed with cyclohexane solution, washed with isopropyl alcohol solution, dehydrated with dehydrating agent, drying at 60-65 °C , finally got o-aminobenzoic acid product anthranilic acid; wherein, the mass fraction of the sodium chloride solution in step (i) is 10-16%, the mass fraction of the cyclohexane solution in the step (i) is 30-40%.2. Drugs intermediates o-aminobenzoic acid synthesis method according to claim 1 wherein the mass fraction of isopropyl alcohol solution in step (i) is 60- 65%.
- 3. Drugs intermediates o-aminobenzoic acid synthesis method according to claim20 1 wherein the dehydrating agent in the step (i) is any one of anhydrous calcium chloride and anhydrous magnesium sulfate.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710071937.1A CN108409588A (en) | 2017-02-09 | 2017-02-09 | A kind of synthetic method of pharmaceutical intermediate ortho-aminobenzoic acid |
| GBGB1705486.7A GB201705486D0 (en) | 2017-02-09 | 2017-04-05 | Drugs intermediates o-aminobenzoic acid synthesis method |
| GBGB1705486.7 | 2017-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2018100390A4 true AU2018100390A4 (en) | 2018-05-10 |
Family
ID=58682491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018100390A Ceased AU2018100390A4 (en) | 2017-02-09 | 2018-03-28 | Drugs intermediates o-aminobenzoic acid synthesis method |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN108409588A (en) |
| AU (1) | AU2018100390A4 (en) |
| GB (1) | GB201705486D0 (en) |
-
2017
- 2017-02-09 CN CN201710071937.1A patent/CN108409588A/en active Pending
- 2017-04-05 GB GBGB1705486.7A patent/GB201705486D0/en not_active Ceased
-
2018
- 2018-03-28 AU AU2018100390A patent/AU2018100390A4/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN108409588A (en) | 2018-08-17 |
| GB201705486D0 (en) | 2017-05-17 |
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|---|---|---|---|
| FGI | Letters patent sealed or granted (innovation patent) | ||
| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |