Reactions of Quinolinium Compounds with Malononitrile and Ethyl

2110

NOTES

VOl. 74

with nitromethane in the presence of base is 1methyl-4-nitromethylenequinolane (IIa), a correc-

s + V

m a

y\c/Z

n

I

,/)A

z

p+ J +d,A '$CHa ". I CH3

369 0

b

315 Z D 0

259

m

I

0

D

c1 Id

-07 'N,

I

CH3

I1 I11 Y = H , Z = SO2; b, Y = C S , Z = CN; c, Y = C S , Z = COOEt d,

c ZGOg D

Q 37 P

70

0

4 6 8 10 12 VOLUME OF AQUEOUS H C O ADDED ( M U

2

I

Fig. 4.-Solubility

of aqueous hydrochloric acid of various concentrations or1 25 xnl. of l,.l-dioxane a t 25 0'. I

l6

I-

1

m 0

m 0

K

IO

REGION OF

NCOMPLETE M,SCIBlLITY

-4

I

146

I I

0 1

2

VOLUME

3 OF

10

4

AQUEOUS

5

6

7

8

H e r ADDED ( M i . )

Fig. 5.--Solubility of aqueous hydrobromic acid of various concentrations in 26.0 nil. of 1,4-dioxaneat 25.0". less than 1.87 AV and hydrobromic acid solutiolis less than :3.64 iV are completely miscible with l,4-dioxane.

Acknowledgment.---The authors are indebted to l k . S. 11:. Kantor, for supplying soiiie of the purified

dioxane employed in this study, and to bIr. L. B. Bronk for analysis of some of the aqueous hydrogen chloride samples. R E S E a R C H 1,ABORATORY

GENERAL ELECTRIC COMPANX

YCIIESECTADX-, Iimv YORK

Reactions of Quinolinium Compounds with Malononitrile and Ethyl Cyanoacetate 13Y X h L b O h

J LEONARD AND ROBERT L. FOSTER

Our finding' that the product resulting from the condensation of 1 -methylquinolinium iodide (1) 'I) h JOT i