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Azasteroids. I. A convenient synthesis of ethyl 1,2,3,3‐tetrahydrohenzo[f] quinoline‐3‐carboxylate
Author(s) -
Popp Frank D.,
Schleigh William R.
Publication year - 1964
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570010211
Subject(s) - chemistry , quinoline , hydrochloric acid , hydrolysis , carboxylate , hydrochloride , acetic acid , catalysis , organic chemistry , medicinal chemistry
In view of the fact that a synthesis of 3‐desoxy‐18‐nor‐14‐azaequilenin (I) has recently been reported (3) we wish to report on our synthetic path to this azasteroid. In this work the intermediate ethyl 1,2,3,4‐tetrahydrobenzo[f]quinoline‐3‐carboxylate (II) was conveniently synthesized from commercially available benzo[f]quinoline (III). Compound III was converted to the Reissert compound (IV) (4), which on hydrolysis (5) gave the acid V. Catalytic hydrogenation of V gave poor results when carried out in glacial acetic acid or 15% hydrochloric acid at room temperature. However, the reduction proceeded smoothly and quantitatively by the procedure indicated in the experimental. Esterification of the crude, reduced acid hydrochloride (VI) proceeded to give II which can be converted into I as described (3).