Hydrochloric Acid → 6-Chloro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

To a solution of 6-chloroquinoline (1.5 g, 9.17 mmol) in C2H5OH (50 ml) was added PtO2 (41.5 mg, 0.18 mmol) and concentrated HCl (0.1 ml) under an atmosphere of hydrogen gas. The reaction was stirred overnight at room temperature, then concentrated in vacuo, diluted with water (100 ml), adjusted to pH 8 with aqueous sodium bicarbonate. The resulting solution was extracted with dichloromethane (3×80 ml) and the organic layers were combined, dried over anhydrous magnesium sulfate, concentrated in vacuo to afford 6-chloro-1,2,3,4-tetrahydroquinoline as a colorless oil (1.2 g, 78%).

Provenance & Evidence