CN110862327A - Preparation method of 5-bromo-2-hydroxyanthranilic acid - Google Patents
Preparation method of 5-bromo-2-hydroxyanthranilic acid Download PDFInfo
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- CN110862327A CN110862327A CN201911098075.7A CN201911098075A CN110862327A CN 110862327 A CN110862327 A CN 110862327A CN 201911098075 A CN201911098075 A CN 201911098075A CN 110862327 A CN110862327 A CN 110862327A
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- China
- Prior art keywords
- mol
- added
- bromo
- acid
- preparation
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- -1 5-bromo-2-hydroxyanthranilic acid Chemical compound 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims abstract description 11
- 239000001632 sodium acetate Substances 0.000 claims abstract description 11
- 235000017281 sodium acetate Nutrition 0.000 claims abstract description 11
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract description 2
- 229940106681 chloroacetic acid Drugs 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- KJZVMBFKUKCLDJ-UHFFFAOYSA-N 5-bromo-2-(hydroxymethyl)benzoic acid Chemical compound OCC1=CC=C(Br)C=C1C(O)=O KJZVMBFKUKCLDJ-UHFFFAOYSA-N 0.000 abstract 1
- SAHQWWLUBRQIEP-UHFFFAOYSA-N BrC=1C=C(C(=C(C(=O)O)C=1)CO)N Chemical compound BrC=1C=C(C(=C(C(=O)O)C=1)CO)N SAHQWWLUBRQIEP-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- JLCRRGUUZISQIS-UHFFFAOYSA-N C1=CC(=C(C=C1Br)C(=O)O)NO Chemical compound C1=CC(=C(C=C1Br)C(=O)O)NO JLCRRGUUZISQIS-UHFFFAOYSA-N 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- 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
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of 5-bromo-2-hydroxymethyl benzoic acid, which removes the step of producing sodium acetate by reacting chloroacetic acid with sodium hydroxide; removing the step of slowly adding bromine in the presence of anthranilic acid under the protection of hydrogen radicals; the method has the advantages of few steps, simple route, mild reaction, high yield, high purity of 95 percent and the like.
Description
Technical Field
The invention relates to a preparation method of 5-bromo-2-hydroxymethyl aminobenzoic acid
Background
5-bromo-2-hydroxyamino benzoic acid with molecular formula of C9N7BrNo4The existing preparation of the p-5-bromo-2-hydroxymethyl aminobenzoic acid has the following defects: (1) the preparation steps are complicated, and the efficiency is low; (2) the energy consumption is high, and the input cost is increased; (3) the yield is low, thereby causing poor economic efficiency.
Disclosure of Invention
Technical problem to be solved
The invention provides a preparation method of 5-bromo-2-hydroxymethyl aminobenzoic acid, which solves the defects.
(II) the adopted technical scheme
In order to achieve the purpose, the invention is realized by the following technical scheme: the preparation method of 5-bromo-2-hydroxyanthranilic acid is characterized by comprising the following steps:
(1) weighing 9g (0.1 mol) of sodium acetate, pouring into 30ml of water, heating to 40 ℃, and slowly dissolving to obtain a sodium acetate aqueous solution for later use;
(2) 14g (0.1 mol) of anthranilic acid is added into a 500ml three-neck flask, 140ml of water is added, 10.6g (0.1 mol) of anhydrous sodium carbonate is added, and the pH value of a stirred solution is 9-10; then slowly adding the prepared sodium acetate aqueous solution into a reaction bottle, wherein the pH value in the reaction bottle is 7-8;
(3) finally, 42.5g (5 mol) of hydrobromic acid is slowly added into the three-neck flask in a dropwise manner for about 1 hour, then the reaction is carried out for 24 hours, solid is separated out from the flask, and the mixture is filtered; washing the filter cake with clear water for 2 times, and drying at 50 ℃ to obtain the product.
(III) advantageous effects
The invention provides a preparation method of 5-bromo-2-hydroxyamino benzoic acid, which has the following beneficial effects:
the invention optimizes the route for synthesizing the 5-bromo-2-hydroxymethyl aminobenzoic acid, and removes the defects of complicated multiple steps, high energy consumption and low yield, so that the method has the advantages of less steps, low energy consumption, high yield and the like.
The invention is optimized from two aspects: (1) the step of producing sodium acetate by reacting chloroacetic acid with sodium hydroxide is eliminated; (2) removing the step of slowly adding bromine in the presence of anthranilic acid under the protection of hydrogen radicals; the method has the advantages of few steps, simple route, mild reaction, high yield and high purity which can reach 95%.
Detailed Description
All of the features disclosed in this specification, or all of the steps in any method or process so disclosed, may be combined in any combination, except combinations of features and/or steps that are mutually exclusive.
Any feature disclosed in this specification (including any accompanying claims, abstract) may be replaced by alternative features serving equivalent or similar purposes, unless expressly stated otherwise. That is, unless expressly stated otherwise, each feature is only an example of a generic series of equivalent or similar features.
Examples
The preparation method of 5-bromo-2-hydroxyanthranilic acid is characterized by comprising the following steps:
(1) weighing 9g (0.1 mol) of sodium acetate, pouring into 30ml of water, heating to 40 ℃, and slowly dissolving to obtain a sodium acetate aqueous solution for later use;
(2) 14g (0.1 mol) of anthranilic acid is added into a 500ml three-neck flask, 140ml of water is added, 10.6g (0.1 mol) of anhydrous sodium carbonate is added, and the pH value of a stirred solution is 9-10; then slowly adding the prepared sodium acetate aqueous solution into a reaction bottle, wherein the pH value in the reaction bottle is 7-8;
(3) finally, 42.5g (5 mol) of hydrobromic acid is slowly added into the three-neck flask in a dropwise manner for about 1 hour, then the reaction is carried out for 24 hours, solid is separated out from the flask, and the mixture is filtered; washing the filter cake with clear water for 2 times, and drying at 50 ℃ to obtain the product.
The method has the advantages of few steps, simple route, mild reaction, high yield and high purity which can reach 95%.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (1)
1. The preparation method of 5-bromo-2-hydroxyanthranilic acid is characterized by comprising the following steps:
(1) weighing 9g (0.1 mol) of sodium acetate, pouring into 30ml of water, heating to 40 ℃, and slowly dissolving to obtain a sodium acetate aqueous solution for later use;
(2) 14g (0.1 mol) of anthranilic acid is added into a 500ml three-neck flask, 140ml of water is added, 10.6g (0.1 mol) of anhydrous sodium carbonate is added, and the pH value of a stirred solution is 9-10; then slowly adding the prepared sodium acetate aqueous solution into a reaction bottle, wherein the pH value in the reaction bottle is 7-8;
(3) finally, 42.5g (5 mol) of hydrobromic acid is slowly added into the three-neck flask in a dropwise manner for about 1 hour, then the reaction is carried out for 24 hours, solid is separated out from the flask, and the mixture is filtered; washing the filter cake with clear water for 2 times, and drying at 50 ℃ to obtain the product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911098075.7A CN110862327A (en) | 2019-11-12 | 2019-11-12 | Preparation method of 5-bromo-2-hydroxyanthranilic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911098075.7A CN110862327A (en) | 2019-11-12 | 2019-11-12 | Preparation method of 5-bromo-2-hydroxyanthranilic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110862327A true CN110862327A (en) | 2020-03-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911098075.7A Pending CN110862327A (en) | 2019-11-12 | 2019-11-12 | Preparation method of 5-bromo-2-hydroxyanthranilic acid |
Country Status (1)
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| CN (1) | CN110862327A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102159589A (en) * | 2008-09-17 | 2011-08-17 | 霍夫曼-拉罗奇有限公司 | Neuropeptide-2 receptor (y-2r) agonists and uses thereof |
-
2019
- 2019-11-12 CN CN201911098075.7A patent/CN110862327A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102159589A (en) * | 2008-09-17 | 2011-08-17 | 霍夫曼-拉罗奇有限公司 | Neuropeptide-2 receptor (y-2r) agonists and uses thereof |
Non-Patent Citations (2)
| Title |
|---|
| REWCASTLE, GORDON W.等: "Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
| 马耀等: "6-溴-4-烃硫基喹啉类化合物的合成及抑菌活性研究", 《有机化学》 * |
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