1,2,3,4-Tetrahydroisoquinoline → HCID 18433086, compound

Participants

Reaction Steps

A solution of 2,4-dichloroquinoline (0.2 g, 1 mmol) and 1,2,3,4-tetrahydroisoquinoline (0.282 ml, 2.2 mmol) in toluene (2 ml) was refluxed during 18 hours then cooled to room temperature. The reaction mixture was diluted with CH2Cl2 and quenched with a saturated solution of NaHCO3. Aqueous phase was extracted with CH2Cl2 (2×). Combined organic phases were washed with H2O, dried over NaSO4, and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate, 97:3) to provide 4-chloro-2-(3,4-dihydro-1H-isoquinolin-2-yl)-quinoline (0.235 g, 79%) as a yellow oil, MS: m/e=295.3 (M+H+).

Provenance & Evidence