
%0 Journal Article
%A Craig, JC 
%A Temple, DM 
%A Moore, B 
%T Simplified Analogues of Lysergic Acid. IV. Synthesis of 1-Methyl-1,2,3,7,8,9,-hexahydro-5,6-benzquinoline
%J Australian Journal of Chemistry
%D 1961/03/01
%V 14
%N 1
%P 84-99
%K 
%R https://doi.org/10.1071/CH9610084
%U https://www.publish.csiro.au/paper/CH9610084 
%X The lysergic acid analogue 1-methyl-1,2,3,7,8,9-hexahydro-5,6-benzquinoline (III ; R=H) was prepared from 2-bromo-&#945;-tetralone by two parallel routes. The first, a seven-stage sequence, involved conversion of the starting material into 2-[N-methyl-N- (2'-oxo-n-propyl)]-amino-&#945;-tetralone (IX) via its ethylene ketal, followed by ring closure to the tricyclic 1-methyl-3-oxo-1,2,3,7,8,9-hexahydro-5,6-benzquinoline (V). This was transformed into its ethylene dithioketal (XXIX) and thence by desulphurization into (III: R=H).   The second pathway, a five-step synthesis, utilized dimethylaminoacetone to obtain directly the quaternary diketone (XXI), which was cyclized to 1,1-dimethyl-3-oxo-1,2,3,7,8,9-hexahydro-5,6-benzquinolinium bromide (XXV), identical with that obtained by the alternative route. 
