Concise Preparation of
Amino-5,6,7,8-tetrahydroquinolines and
Amino-5,6,7,8-tetrahydroisoquinolines via
Catalytic Hydrogenation of
Acetamidoquinolines and
Acetamidoisoquinolines
posted on 2002-10-03, 00:00authored byKrystyna A. Skupinska, Ernest J. McEachern, Renato T. Skerlj, Gary J. Bridger
A method to prepare amino-substituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydroisoquinolines via
catalytic hydrogenation of the corresponding acetamido-substituted quinolines and isoquinolines followed by acetamide hydrolysis is described. The yields of the products are
good when the acetamido substituent is present on the
pyridine ring and moderate with the acetamido substituent
on the benzene ring. This method has also been applied to
the regioselective reduction of quinoline substrates bearing
other substituents (R = OMe, CO2Me, Ph).