1-Chloroanthraquinone → Anthrimide

HRID 542992

Reaction equation

Cl[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[CH:5]=[CH:4][CH:3]=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[CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]Cl>[CH:10]1[CH:9]=[C:8]2[C:7]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:18][C:19]4[C:32]5[C:31]([C:30]6[C:25]([C:24](=[O:34])[C:23]=5[CH:22]=[CH:21][CH:20]=4)=[CH:26][CH:27]=[CH:28][CH:29]=6)=[O:33])[C:15]=3[C:14](=[O:16])[C:13]2=[CH:12][CH:11]=1)=[O:17]

Participants

Conditions

Temperature: 190 °C

Procedure

66 parts of 1-chloroanthraquinone, 60.5 parts of 1-aminoanthraquinone, 26.4 parts of sodium carbonate and 0.75 part of copper(I) chloride are suspended in 550 parts of nitrobenzene. With stirring, the mixture is heated to 190° C. and then a further 0.75 part of copper(I) chloride is added. The reaction mixture is heated to 206° C. and stirred for 3 hours at this temperature while distilling off the water of reaction. The batch is then heated to 214° C. and the pressure rises to about 1 bar. Stirring is continued for another 2 hours under these conditions. The reaction mixture is then cooled slightly and the nitrobenzene is removed by distillation. After drying there are obtained about 115 parts of anthrimide, which is suitable for further processing to give vat dyes.

Workup

temperatureThe reaction mixture is heated to 206° C.
stirringstirred for 3 hours at this temperature
distillationwhile distilling off
customthe water of reaction
temperatureThe batch is then heated to 214° C.
stirringStirring
temperatureThe reaction mixture is then cooled slightly
customthe nitrobenzene is removed by distillation
customAfter drying there

Sources & evidence

ORD record: ord-9c2fec673e5f4601a85c0970a6f0fdfc
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659831

Linked notes

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