Nitrobenzene → 1-(2-Chloro-4-nitroanilino)-5-methoxyanthracene-9,10-dione

Participants

Reaction Steps

12.65 parts of 1-amino-5-methoxyanthraquinone, 15.3 parts of 1-bromo-2-chloro-4-nitrobenzene, 5 parts of sodium carbonate and 1 part of copper-(I) chloride in 120 parts of nitrobenzene are stirred for 3 hours at 170°. To remove the water formed during the reaction, a stream of nitrogen is passed through the apparatus during the reaction. After cooling the reaction mixture to 25°, the 1-(2'-chloro-4'-nitroanilino)-5-methoxyanthraquinone formed is filtered off, washed with nitrobenzene, ethanol and hot water and extracted by boiling with 5% strength hydrochloric acid. The colorant is obtained in a yield of 19.5 parts, that is to say 95% of theory. It bulk-dyes polyester in an orange-coloured shade having excellent fastness properties.

Provenance & Evidence