2-Phenylquinoline-7-carbaldehyde → 7-Methyl-2-phenylquinoline

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Reaction Steps

Additionally, 2-phenylquinoline-7-carbaldehyde could be prepared as follows: To a solution of(2-phenylquinolin-7-yl)methanol (75 mg, 0.319 mmol) in chloroform (1 mL) was added MnO2 (277 mg, 3.19 mmol). The mixture was stirred at rt for 20 h and filtered through a Celite pad. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography. (1% MeOH in dichloromethane) to afford the title compound. 1H-NMR (CDCl3, 400 MHz) δ 7.50-7.59 (m, 3H), 7.95 (d, J=8.8 Hz, 1H), 8.04 (dd, J=2.4, 8.8 Hz, 2H), 8.19-8.22 (m, 2H), 8.31 (d, J=8.8 Hz, 1H), 8.69 (s, 1H), 10.26 (s, 1H). MS (ES+): m/z 234 [MH+]. HPLC: tR=3.59 min (OpenLynx, polar—5 min).

Provenance & Evidence