Hydrochloric Acid → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

Participants

Reaction Steps

Thirty-five grams of 8-amino-1,2,3,4-tetrahydroquinoline was dissolved in methanol (700 mL) and, following the addition of 3-phenylpropionaldehyde (37.4 mL) and 1N HCl (7 mL) and subsequent stirring at room temperature for 1 hr, silica gel (75 g) was added to the reaction solution and the solvent was removed under reduced pressure. The residue was heated at 100° C. for 1 hr, purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate) and recrystallized with ethyl acetate to yield the titled compound as pale yellow crystals (19.3 g).

Provenance & Evidence