
TY  - JOUR
A1  - Craig, JC 
A1  - Temple, DM 
A1  - Moore, B 
T1  - Simplified Analogues of Lysergic Acid. IV. Synthesis of 1-Methyl-1,2,3,7,8,9,-hexahydro-5,6-benzquinoline
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1961
VL  - 14
IS  - 1
SP  - 84
EP  - 99
KW  - 
UR  - https://doi.org/10.1071/CH9610084 
N2  - 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. 
ER  -

