Sodium Bicarbonate → 4-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile

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A mixture of 6.20 g (26.6 mmol) of 4-chloro-6-nitroquinoline-3-carbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of EtOH was refluxed under N2 for 5 hr. Satd NaHCO3 was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and H2O and dried. The insoluble material was repeatedly extracted with boiling EtOAc and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of 4-(3,4-dibromophenylamino)-6-nitroquinoline-3-carbonitrile as a green solid: mass spectrum (electrospray, m/e): M+H 448.9.

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