
%0 Journal Article
%A Bowie, JH 
%A Hayes, RN 
%A Mitkas, S 
%A Prager, RH 
%A Raftery, MJ 
%A Skelton, BW 
%A Stringer, MB 
%A White, AH 
%T 1-Benzazepines. The Synthesis and Reactivity of 2-Chloro-1,5-Dimethyl-1h-1-Benzazepines
%J Australian Journal of Chemistry
%D 1986/03/01
%V 39
%N 3
%P 529-539
%K 
%R https://doi.org/10.1071/CH9860529
%U https://www.publish.csiro.au/paper/CH9860529 
%X Treatment of laevulinic acid with N- methylaniline yields 1,5-dimethyl- 1H-1-benzazepin-2(3H)-one and 5-methyl-5-[4-( methylamino )phenyl]-1- phenylpyrrolidin-2-one. The structure of the latter is confirmed by a single-crystal X-ray study. The yield of benzazepinone is increased if either m- methoxy-N-methylaniline or m-methyl-N- methylaniline is allowed to react with laevulinic acid. Treatment of the benzazepinones with phosphoryl chloride in pyridine produces 2-chloro-1,5-dimethyl-1H-1- benzazepines in quantitative yields, but these compounds are highly reactive under acidic conditions, undergoing nucleophilic displacement at C2. In contrast, treatment of benzazepinones with neat phosphoryl chloride yields yellow dimers , assigned as 2&#8242;-chloro-1,1&#8242;,5,5&#8242;- tetramethyl-2,3&#8242;-bi-1H-1-benzazepines, and with stabilities only marginally greater than those of the 2-chloro-1,5-dimethyl-1H-1- benzazepines. 
