Aug., 1040
8-(5-ISOPROPYLAMINOAMYLAMINO)-O-METrIoXYo,UINoI,INE
1529
The chloroform solution thus obtained was e x t r a c 3 nitroquinoline, 100 ml. of water, 5 ml. of glacial acetic acid, with an equal volume of 1 M citric acid. The extract was 1 ml.of dibutyl ether and 10 g. of iron filings was heated made strongly alkaline and extracted with ether. The under reflux with stirring on the steam-bath for seventeen material extracted by the ether, after drying, was distilled, hours. The mixture was filtered, the filtrate was made the part boiling at 190-195" (0.15 mm.) being collected. basic and filtered again. The precipitate was washed once The recovery was 19 g. (60%). After conversion t o the with acetone, and the combined aqueous filtrate and aceoxalate, the drug was re-examined by the 8-plate technique tone washings were extracted three times with ether. The and showed the presence of 370 of the more basic inhomo- solid residue from the acetone wash was extracted three geneity and 27, of the less basic inhon~ogeneity,which is . times with boiling acetone and filtered after each extraction. The material from the combined acetone and ether within acceptable limits. Reduction of 8-Nitroquinoline Derivatives. ( a ) With extracts, after drying, was distilled, the fraction boiling a t 172-175" (22 mm.) being collected. The distillate was reStannous Chloride.-This method has been described in detail in a preceding paper.6 If the aminoquinoline was a crystallized from alcohol. The properties of the various 8-aminoquinolines are liquid, it was extracted with ether or chloroform. The material obtained on removal of the solvent was used di- given in Table 11. In all cases & is "2. rectly. Summary (b) With Iron. and Acetic Acid.-In the case of tht: reduction of 7-niethyl-8-nitroquinoline by method (a), some 1. The synthesis of fifty-one analogs of nuclear chlorination occurred despite all precautions. Pamaquine (Plasmochin) has been described. Pure 7-methyl-8-aminoquinolinewas obtained by use of 2 . The synthesis of five new derivatives of Siron and acetic acid.28 A mixture of 10 g. of 7-methyl-8-
aminoquinoline has been described. RECEIVED APRIL 5, 1946 SEW YORK37, S . Y.
(26) Private communication from Dr. Walter Lauer of the University of Minnesota. -
[ C U K T R I B E T i O K FROM
THE
LABORATORIES O F THE
USIVERSITY OF
h'f ARYLAND]
Synthetic Antimalarials. 8-(5-Isopropylaminoamylamino)-6-methoxyquhol~ne (SN13,276)l and Some.Related Compounds2 BY NATHANL. DRAKE,JOHN VAN HOOK,J o I m A. GARMAN, ROBERTHAYES,K.JOHNSON, G. K E L L E Y , S I D N E Y b I E L A h l E D AND I
