4-Fluoroaniline → HCID 178512263, compound

Participants

Reaction Steps

Diphenyl cyanocarbonimidate (0.24 g, 1.0 mmol) and 4-fluoroaniline (104 4μL, 1.1 mmol) are stirred in isopropanol (10 mL) for 15 h. The reaction mixture is concentrated, and the residue dissolved in EtOAc. Washing with sat NaHCO3, drying (MgSO4) and removing the solvent delivers 0.34 g of N-cyano-N′-(4-fluorophenyl)-O-phenylisourea as a colorless solid. It is dissolved in pyridine (15 mL) and 7-chloro-4-(piperazin-1-yl)quinoline (0.25 g, 1.0 mmol) is added. The reaction mixture is heated at reflux for 4 h and afterwards concentrated. Column chromatography of the residue with hexane-EtOAc gives the title product as a colorless solid.

Provenance & Evidence