Nitrobenzene → 1-Amino-2-bromo-4-benzoylaminoanthraquinone

HRID 1680797

Reaktionsgleichung

[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]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[N+](C1C=CC=CC=1)([O-])=O.[Br:36]Br.S([O-])(O)=O.[Na+]>O>[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]([NH:18][C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][C:3]=1[Br:36]

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

With stirring, 85.5 parts of 1-amino-4-benzoylaminoanthraquinone are suspended in 200 parts of nitrobenzene. The suspension is diluted with 100 parts of water and then a solution of 50.4 parts of bromine in 60 parts of nitrobenzene is added in the course of 1 hour at 30°-35° C. The reaction is brought to completion by stirring for 3 hours at 50°-55° C. The mixture is cooled to 30°-35° C. and, after addition of 65 parts of a 40% sodium hydrogen sulfite solution, stirred for 1/2 hour and cooled to 20° C. Finally, the reaction product is collected by suction, washed with 60 parts of nitrobenzene as well as with ethanol and hot water, and dried, affording 91 parts (86.5% of theory) of 1-amino-2-bromo-4-benzoylaminoanthraquinone with a melting point of 241° C.-243° C. Br: calculated 18.97%, found 18.5%.

Aufarbeitung

stirringby stirring for 3 hours at 50°-55° C
temperatureThe mixture is cooled to 30°-35° C.
stirringstirred for 1/2 hour
customFinally, the reaction product is collected by suction
washwashed with 60 parts of nitrobenzene as well as with ethanol and hot water
customdried

Quellen und Nachweise

ORD-Eintrag: ord-05f6d7e92b9f4668bbfd54d19f387864
Quelldatensatz: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04276213

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