Premium
3‐(Arylamino)quinolin‐2(1 H )‐ and ‐4(1 H )‐ones: Reinvestigation of the Reaction between Ethyl 2‐Chloro‐3‐(phenylamino)but‐2‐enoate and Arylamines
Author(s) -
Fretz Heinz,
Gaugler Markus,
Schneider Joseph
Publication year - 2000
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 - 10.1002/1522-2675(20000607)83:6<1145::aid-hlca1145>3.0.co;2-j
Subject(s) - chemistry , aniline , heteronuclear single quantum coherence spectroscopy , nuclear magnetic resonance spectroscopy , medicinal chemistry , alkyl , proton nmr , stereochemistry , organic chemistry
The reaction between ethyl 2‐chloro‐3‐(phenylamino)but‐2‐enoate ( 5 ) and aniline gave 4‐methyl‐3‐(phenylamino)quinolin‐2(1 H )‐one ( 6 ) and not, as reported earlier in the literature, the isomeric 2‐methyl‐3‐(phenylamino)quinolin‐4(1 H )‐one ( 1 ). The latter could be prepared by an alternative procedure. The structures of both isomers were established by extensive NMR spectroscopy including 1D‐NOE, 2D‐HSQC, and HMBC experiments. Consequently, the reinvestigation of the title reaction revealed an unexpected simple access to novel 4‐alkyl‐substituted 3‐(arylamino)quinolin‐2(1 H )‐ones.