Pyridine → Isopropyl 1-amino-4-bromoanthraquinone-2-carboxylate

HRID 1647015

Reaktionsgleichung

Reaktionsgleichung von HRID 1647015
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([Br:18])=[CH:4][C:3]=1[C:19]([OH:21])=[O:20].S(Cl)(Cl)=O.N1C=C[CH:29]=[CH:28][CH:27]=1.ClC1C=CC=CC=1Cl>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1.ClC1C=CC=CC=1>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([Br:18])=[CH:4][C:3]=1[C:19]([O:21][CH:28]([CH3:29])[CH3:27])=[O:20]

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 72391,2-DichlorobenzeneHCID 24386Thionyl ChlorideHCID 2715931-Amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Produkt 1

HCID 19800488Isopropyl 1-amino-4-bromoanthraquinone-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 7237O-XyleneLösungsmittelHCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

The starting 1-amino-4-bromoanthraquinone-2-carboxylic acid is reacted with 1.5 to 3 molar equivalents of a chlorinating agent such as thionyl chloride at a temperature of 80° to 100° C. for a period of about 1 to 3 hours in the presence of 0.01 to 5 molar equivalents (based on the raw material) of pyridine in 3 to 7-fold weight a amount of an inert solvent such as orthodichlorobenzene, chlorobenzene, toluene or xylene so as to be converted into an acid chloride. After the excess chlorinating agent has been removed therefrom under reduced pressure, 1.5 to 5 molar equivalents of isopropyl alcohol is added thereto and esterification is then performed at 60° to 80° C. for 1 to 3 hours. Afterward, the product is allowed to stand, thereby obtaining crystals of isopropyl 1-amino-4-bromoanthraquinone-2-carboxylate.

Aufarbeitung

  1. customAfter the excess chlorinating agent has been removed
  2. additionunder reduced pressure, 1.5 to 5 molar equivalents of isopropyl alcohol is added

Quellen und Nachweise

ORD-Eintrag
ord-6794cf50d8644b1f9d0bd07864d3b5a3
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05182395

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