“…The ability of quinoline to react with an acid chloride and a source of cyanide ion to form I is greatly affected by substituents present on the ring. 6-Methoxyquinoline (37), 6-chloroquinoline (35), 6-methylquinoline (35), and 7-methoxyquinoline (86) readily undergo reaction with benzoyl chloride and aqueous potassium cyanide to give the respective substituted derivatives of 1-benzoyl-l, 2-dihydroquinaldonitrile (I: R = C6H5), but when the substituent is the 5-nitro, 5-amino, 5-acetamido, 6-dimethylamino, 7-nitro, 8-hydroxy, 8-methoxy, 8benzoyloxy, 8-acetoxy, or 2-methyl group, the reaction fails (37). Reaction of benzoyl chloride and aqueous potassium cyanide with 2, 3'-biquinoline gives l-benzoyl-3-(2-quinolyl)-1,2-dihydroquinaldonitrile (VII) (48), while reaction with 6,6'-biquinoline gives 1,1'-dibenzoyl-1,1',2,2'-tetrahydro-6,6'-biquinaldonitrile (VIII) (91).…”