1-Amino-2,4-dibromoanthraquinone → 1-Amino-2-bromo-4-hydroxyanthraquinone

HRID 1905847

Reaktionsgleichung

Reaktionsgleichung von HRID 1905847
NC1C2C(=[O:16])C3C(=CC=CC=3)C(=O)C=2C=CC=1.[NH2:18][C:19]1[C:32]2[C:31](=[O:33])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:34])[C:23]=2[C:22](Br)=[CH:21][C:20]=1[Br:36].B(O)(O)O>S(=O)(=O)(O)O>[NH2:18][C:19]1[C:32]2[C:31](=[O:33])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:34])[C:23]=2[C:22]([OH:16])=[CH:21][C:20]=1[Br:36]

Komponenten

5

Edukt 3

HCID 66811-Amino-2,4-dibromoanthraquinoneHCID 67101-AminoanthraquinoneHCID 7628Boric Acid

Produkt 1

HCID 83201-Amino-2-bromo-4-hydroxyanthraquinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Further, German Offenlegungsschrift No. 28 17 890 discloses a one-vessel process and starting from 1-aminoanthraquinone, which is first converted by bromination into 1-amino-2,4-dibromoanthraquinone, which is in turn, without being isolated, reacted in sulfuric acid, in the presence of boric acid, to give 1-amino-2-bromo-4-hydroxyanthraquinone. The process is simple to perform and affords the desired product in good yield. The shortcoming of this process is, however, that the mixture of dilute sulfuric acid and boric acid formed during working up cannot be easily regenerated. For example, glassy residues are obtained and it is often necessary to neutralise the waste sulfuric acid, e.g. with calcium carbonate or slaked lime. In addition, the 1-amino-2-bromo-4-hydroxyanthraquinone obtained by this process is contaminated by compounds that are brominated in the 3-position. Such impurities result in changes in shade during the dye synthesis, i.e. standard shade dyes are not obtained.

Aufarbeitung

  1. customwithout being isolated

Quellen und Nachweise

ORD-Eintrag
ord-72b0a6a90ab0450ba542b365630340af
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04648994

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