Abstract
Hydrogenation of pyridyl and quinolyl compounds 2-substituted with a carbonyl group ( 1a– c and 2b, c ) using PtO 2 and 1 equiv. of HCl (conditions A) provides clean and total formation of the desired amino alcohol (hydrogenation of the heterocyclic ring and of the carbonyl) while under conditions B 1 and/or B 2 (concentrated HCl or pure CF 3CO 2H) the heterocyclic ring remains untouched and other aromatic parts are hydrogenated providing complex mixtures. When the heterocyclic ring is substituted by an alkyl group (quinaldine 3 ) conditions A provide mixtures while under conditions B 2 (pure CF 3CO 2H) the benzene ring is cleanly hydrogenated leading to a pure product.
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