Aniline → 8-bromo-N-phenylquinolin-2-amine

Participants

Reaction Steps

To a solution of aniline (0.76 g, 8.16 mmol) and 8-bromo-2-chloroquinoline (Biofine International, Vancouver, BC; 1.1 g, 4.54 mmol) in THF (7 mL) at 0° C. was added LiHMDS (1.0 M solution in THF, 13.61 mL, 13.61 mmol) drop wise via a syringe. The resulting brown mixture was stirred at RT for 1 h, and then quenched with sat. NH4Cl solution (15 mL) and extracted with EtOAc (2×50 mL). The combined organic solution was concentrated and the residue was purified on a silica gel column (25-45% EtOAc in hexanes) to afford 8-bromo-N-phenylquinolin-2-amine (Ex. 165c, 1.03 g, 3.44 mmol, 76% yield) as a brown crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.69 (1H, s), 8.21 (2H, d, J=7.8 Hz), 8.10 (1H, d, J=8.8 Hz), 7.94 (1H, m), 7.77 (1H, d, J=7.0 Hz), 7.35 (2H, t, J=7.8 Hz), 7.21 (1H, t, J=7.7 Hz), 7.13 (1H, d, J=9.0 Hz), 6.98 (1H, t, J=7.3 Hz). m/z (ESI, +ve) 299/301 (M+H)+.

Provenance & Evidence