3-Chloroacetanilide → N-[3-(Dibutylamino)phenyl]acetamide

Participants

Reaction Steps

An oven-dried resealable schlenk tube containing a stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (11.9 mg, 0.025 mmol), 3-chloroacetanilide (85 mg, 0.5 mmol) and sodium tbutoxide (120 mg, 1.25 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. Dinbutylamine (126 μL, 0.75 mmol) and tbutanol (1 mL) were added through the septum via syringe. The septum was replaced with a Teflon screw cap. The schlenk tube was sealed and put into a pre-heated oil bath at 90° C. The reaction mixture was stirred for 18 h, allowed to cool down to room temperature and quenched with water. Extraction with ethyl acetate three times followed by chromatography on silica gel column with 4:1 hexane:ethyl acetate gave 106 mg (81%) of the title compound as a pale yellow oil.

Provenance & Evidence