- Preparation process for sodium 1-amino-4-bromoanthraquinone-2-sulfonate
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The invention discloses a preparation process for sodium 1-amino-4-bromoanthraquinone-2-sulfonate. The preparation process comprises the following steps: (1) sulfonation: with 1-aminoanthraquinone as a raw material, copper sulfate as a catalyst and dichloroethane as a solvent, carrying out dehydration, then adding chlorosulfonic acid drop by drop for a sulfonation reaction, adding 98% concentrated sulfuric acid after completion of the reaction, extracting 1-aminoanthraquinone-2-sulfonic acid out, allowing 1-aminoanthraquinone-2-sulfonic acid to enter the concentrated sulfuric acid, separating out an acid phase at a lower layer and subjecting the acid phase to a subsequent reaction; (2) bromination: adding bromine into the concentrated sulfuric acid solution of 1-aminoanthraquinone-2-sulfonic acid drop by drop for a reaction so as to obtain the concentrated sulfuric acid solution of bromoamine acid; (3) dilution: adding water into the concentrated sulfuric acid solution of bromoamine acid for dilution and successively carrying out cooling, crystallization and filtering so as to obtain bromoamine acid; and (4) salt formation: adding water to dissolve bromoamine acid and adding sodium sulfite to obtain bromoamine acid sodium salt. The preparation process provided by the invention can reduce energy consumption during solvent recovery; the utilization rate of bromine in bromination is high; sodium sulfite is used for salt formation, so the amount of impurities is reduced; and product quality is high.
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Paragraph 0010
(2016/12/26)
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- Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs
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Anthraquinone (AQ) derivatives play a prominent role in medicine and also in textile industry. Bromaminic acid (1-amino-4-bromoanthraquinone-2-sulfonic acid) is an important precursor for obtaining dyes as well as biologically active compounds through the replacement of the C4-bromo substituent with different (ar)alkylamino residues. Here we report methods for the synthesis of bromaminic acid analogues bearing different substituents at the 2-position of the anthraquinone core. 1-Aminoanthraquinone was converted to its 2-hydroxymethyl-substituted derivative which, under different reaction conditions, yielded the corresponding carbaldehyde, carboxylic acid, and nitrile derivatives. The latter was further reacted to obtain 1-amino-2-tetrazolylanthraquinone. Subsequent bromination using bromine in DMF led to the corresponding bromaminic acid derivatives in excellent isolated yields (>90%) and high purities. Alternatively, 1-amino-4-bromo-2-hydroxymethylanthraquinone could be directly converted to the desired 2-substituted bromaminic acid analogues in high yields (85-100%). We additionally report the preparation of bromaminic acid sodium salt and 1-amino-2,4-dibromoanthraquinone directly from 1-aminoanthraquinone in excellent yields (94-100%) and high purities. The synthesized brominated AQs are valuable precursors for the preparation of AQ drugs and dyes.
- Malik, Enas M.,Baqi, Younis,Müller, Christa E.
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supporting information
p. 2326 - 2333
(2016/02/12)
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- OPTIMIZATION OF THE OXIDATIVE BROMINATION OF 1-AMINOANTHRAQUINONE-2-SULFONIC ACID
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An efficient method of synthesis of 1-amino-4-bromoanthraquinone-2-sulfonic acid using bromination of the corresponding aminoathraquinonesulfonic acid with bromine in the presence of hydrogen peroxide has been proposed.The optimum conditions of synthesis, with a yield of the target product of 68percent, have been found.
- Gerasimov, S. V.,Filimonov, V. D.
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p. 928 - 930
(2007/10/03)
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- Process for separating off 1-amino-4-bromoanthraquinone-2-sulphonic acid
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A process for separating off 1-amino-4-bromoanthraquinone-2-sulphonic acid from the reaction mixture formed by the bromination of 1-aminoanthraquinone-2-sulphonic acid in sulphuric acid, which process comprises adjusting the sulphuric acid concentration of the reaction mixture under the prevailing conditions of temperature and pressure to effect precipitation of 1-amino-4-bromoanthraquinone-2-sulphonic acid as the sulphate and thereafter separating the resultant sulphate precipitate from the reaction mixture.
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