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

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:3])[CH3:2].C(OCC)(=O)C.CCCCCC>C(O)C.[Pd]>[CH3:2][C:1]([NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH2:6]1)=[O:3]

Participants

Procedure

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.