Dimethylformamide → 1,2,3,4-Tetrahydroquinoline-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-1,2,3,4-tetrahydroquinoline (10 g, 47.15 mmol) in N,N-dimethylformamide (80 mL) was added Pd(PPh3)4 (2.8 g, 2.42 mmol), and zincdicarbonitrile (6.4 g, 54.49 mmol) and the reaction was stirred for 2 h at 120° C. in an oil bath. The reaction was quenched by the addition of water (400 mL) and extracted with dichloromethane (3×50 mL), and concentrated in vacuo to give a residue, which was purified by a silica gel chromatography with 1%-20% ethyl acetate in petroleum ether to give 1,2,3,4-tetrahydroquinoline-6-carbonitrile as a yellow solid (6 g, 80%).

Provenance & Evidence