Australian Journal of Chemistry

Simplified Analogues of Lysergic Acid. IV. Synthesis of 1-Methyl-1, 2, 3, 7, 8, 9,-hexahydro-5, 6-benzquinoline

JC Craig, DM Temple, B Moore

Index: Cymerman Craig,J. et al. Australian Journal of Chemistry, 1961 , vol. 14, p. 84 - 99

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Citation Number: 4

Abstract

Abstract The lysergic acid analogue 1-methyl-1, 2, 3, 7, 8, 9-hexahydro-5, 6-benzquinoline (III; R= H) was prepared from 2-bromo-α-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-α-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 ...