Collect. Czech. Chem. Commun. 1979, 44, 2238-2242

Reduction of 2-, 3- and 4-quinolinecarbonitrile and 3- and 4-quinolinecarbonitrile methyl methosulfates with triethylammonium formate

Miloslav Ferles and Oldřich Kocián

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Whereas 2-quinolinecarbonitrile (Ia) is not reduced with triethylammonium formate, 3-quinolinecarbonitrile (Ib) affords a mixture of 1,4-dihydro-3-quinolinecarbonitrile (IVb) and 1-formyl-1,2,3,4-tetrahydroquinoline-3-carboxamide (IIa) in addition to the corresponding acid IIb. 4-Quinolinecarbonitrile (Ic) is reduced to 1-formyl-1,2,3,4-tetrahydroquinoline-4-carbonitrile (IId) and 1-formyl-1,2,3,4-tetrahydroquinoline (IIc). Reduction of 3-quinolinecarbonitrile methyl methosulfate (Va) at low temperature leads to 1-methyl-1,4-dihydroquinoline-3-carbonitrile (IVc) whereas at higher temperatures it affords, in addition to IVc, 1-methyl-1,2,3,4-tetrahydroquinoline-3-carboxamide (IIf) and the acid IIg. 4-Quinolinecarbonitrile methyl methosulfate (Vb) gives 1-methyl-1,2,3,4-tetrahydroquinoline-4-carbonitrile (IIh) and 1-methyl-1,2,3,4-tetrahydroquinoline (IIe).