Hydrochloric Acid → 1,4-Cyclohexadiene-1,4-dicarboxylic acid, 2,5-bis((4-chlorophenyl)amino)-, 1,4-dimethyl ester

Participants

Reaction Steps

Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate (4.5 6 gm; 20 mmol) and methanol (100 ml) were heated to boiling; then 4-chloroaniline (5.36 gm; 42 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 8.62 gm (96%) of dimethyl 2,5-bis{(4-chlorophenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylate.

Provenance & Evidence