Benzaldehyde → 8-Methyl-2-phenylquinoline-4-carboxylic acid

Participants

Reaction Steps

A solution of 2-methylaniline (1.07 g, 1.07 mL, 10.0 mmol), pyruvic acid (0.88 g, 0.70 mL, 10.0 mmol), and benzaldehyde (1.06 g, 1.01 mL, 10.0 mmol) in absolute ethanol (50 mL) was stirred at reflux for 3 h. After cooling, the solvent was removed in vacuo to give 3.52 g of a yellow paste, which was triturated with successive fresh portions of hexanes (3×100 mL). The solid was collected by filtration and airdried to yield the title compound (1.21 g) as a yellow-orange solid, which was used without further purification. MS (API+): M+1: 309 (100%).

Provenance & Evidence