Sodiumniethoxide, potassium hydroxide, and ammonia, as nucleophilic reagents, replaced the 7-fluorine atom in 5,6,7,8tetrafluoroquinoline. Some of the reactions of these derivatives are described. WITH the exception of the 4-fluoro-compound all the monofluoro-derivatives of quinoline have been prepared by means of the Balz-Schiemann reaction on the corresponding aminoquinolines.1 Decomposition of both the diazonium fluorosilicate and the diazonium fluoride in anhydrous hydrogen fluoride has been used to prepare 2-fluoroquinoline.2 This compound has also been prepared by the reaction of anhydrous potassium fluoride with 2-chloroquinoline in dimethyl s ~l p h o x i d e . ~ The Skraup synthesis has beeil used to prepare 6-, T-, and S-fluoroquinoline, using the appropriate flu~roanilines,~ 9%-fluoroaniline giving only the 'i-fluoro-and no 5-fluoro-quinoline. The only difluoroquinoline mentioned in the literature is the 2,4-derivative prepared from 4-hydroxy-2-quinolone by fluorination nith trifluor0-1,2,5-triazine.~l i e report here the syntheses of 5,G,'i,S-tetrafluoroquinoline and 2-and 4-methyl-5,6,7,8-tetrafluoroyuinoline by Skraup reactions of 8,3,4,5-tetrafluoroaniline with glycerol, crotonaldehyde, and methyl vinyl ketone, respectively, and we have studied some of the properties of 5,6,7,8-t e trafluoroquinoline. I n contrast to the parent hydrocarbon, this tetrafluoroquinoline had only weakly basic properties; it formed a hydrochloride only under anhydrous conditions, which shows