
TY  - JOUR
A1  - Bowie, JH 
A1  - Hayes, RN 
A1  - Mitkas, S 
A1  - Prager, RH 
A1  - Raftery, MJ 
A1  - Skelton, BW 
A1  - Stringer, MB 
A1  - White, AH 
T1  - 1-Benzazepines. The Synthesis and Reactivity of 2-Chloro-1,5-Dimethyl-1h-1-Benzazepines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1986
VL  - 39
IS  - 3
SP  - 529
EP  - 539
KW  - 
UR  - https://doi.org/10.1071/CH9860529 
N2  - 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. 
ER  -

