4-Chloroaniline → HCID 23132421, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloroaniline (2.55 g, 20 mmol), N-(6-bromohexyl)-phthalimide (6.20 g, 20 mmol) and K2CO3 (2.76 g, 20 mmol) were suspended in DMF (50 mL) under an atmosphere of argon and stirred at 90° C. for 25 h. The solvent was evaporated under reduced pressure and the residue was partitioned between water (100 mL) and Et2O (100 mL). The aqueous layer was extracted with Et2O (2×50 mL), the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (EtOAc/hexane 1:6 to 1:3) to give the title compound (3.41 g), together with some 4-chloroaniline (≈2:1).

Provenance & Evidence