Hydrochloric Acid → Dimethyl-2,5-bis[(4-bromophenyl)amino]cyclohexa-1,4-diene-1,4-dicarboxylate

Participants

Reaction Steps

Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate (4.56 gm; 20 mmol) and methanol (100 ml) were heated to boiling, then 4-bromoaniline (6.88 gm; 40 mmol) was added followed by conc. hydrochloric acid (200 μl). The mixture was refluxed for 5 hours under a nitrogen atmosphere. On cooling a cream solid precipitated out which was collected by filtration, washed with methanol and dried under vacuum to give 10.18 gm (95%) of dimethyl 2,5-bis{(4-bromophenyl)amino}cyclohexa-1,4-diene-1,4-dicaboxylate.

Provenance & Evidence