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Azidiniumsalze. 7. Mitteilung [1]. Synthese von 1‐Äthyl‐2‐azido‐6‐X‐chinolinium‐fluoroboraten
Author(s) -
Balli H.,
Schelz D.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530741
Subject(s) - chemistry , sodium azide , tetrafluoroborate , quinoline , medicinal chemistry , substituent , methanol , alkylation , sodium nitrite , hydrochloric acid , sodium , ring (chemistry) , sodium methoxide , nitro , organic chemistry , alkyl , ionic liquid , catalysis
6‐X‐Quinolines (X = CH 3 , C 6 H 5 , CO 2 C 2 H 5 , Cl, Br) are successively transformed into 1‐methyl‐6‐X‐carbostyrils, 2‐chloro‐6‐X‐quinolines and 1‐ethyl‐2‐chloro‐6‐X‐quinolinium‐tetrafluoroborates; the latter are transformed into the title compounds by reaction with sodium azide in methanol. 2‐Chloro‐6‐acetamido‐quinoline is alkylated at two positions: at the nitrogen atom of the heterocyclic ring and obviously at the oxygen atom of the 6‐substituent; with sodium azide in methanol the product of alkylation yields 1‐ethyl‐2‐azido‐6‐amino‐quinolinium‐tetrafluoroborate. 1‐Ethyl‐2‐azido‐6‐nitro‐quinolinium‐tetrafluoroborate is obtained by treating 1‐ethyl‐2‐hydrazino‐6‐nitro‐quinolinium‐chloride with sodium tetrafluoroborate and sodium nitrite in diluted hydrochloric acid.