3-Acetylaminoquinoline → N-(1,2,3,4-tetrahydroquinolin-3-yl)acetamide

Participants

Reaction Steps

300 mg of the 3-(acetylamino)quinoline (Rf (D)=0.43) obtained by a single recrystallization from ethyl acetate/hexane are hydrogenated in 10 ml of ethanol in the presence of 60 mg of palladium-on-charcoal (10% of Pd) at 50° C. under normal pressure for 20 h. After the reaction mixture has been filtered over Celite® 545 and the crude product has been purified by chromatography over 25 g of silica gel (mobile phase P), 3(R,S)-methylcarbonylamino-1,2,3,4-tetrahydroquinoline is obtained: Rf (P)=0.49; MS: (M)+ =190.

Provenance & Evidence