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An unexpected product during synthesis of 3‐phenylisoquinoline: Improved preparation of 4‐hydroxy‐3‐phenylisoquinoline
Author(s) -
Sard Howard
Publication year - 1994
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.5570310466
Subject(s) - chemistry , yield (engineering) , allylic rearrangement , product (mathematics) , reaction conditions , combinatorial chemistry , organic chemistry , catalysis , geometry , mathematics , metallurgy , materials science
During repetition of the Bradsher procedure for the preparation of 3‐phenylisoquinoline ( 1 ) an unexpected by‐product was isolated, 4‐hydroxy‐3‐phenylisoquinoline ( 3 ). This product is likely formed via allylic oxidation of a 1,4‐dihydroisoquinoline intermediate. By minor modification of the reaction conditions, 3 can be obtained in up to 50% yield. This represents a much improved method for the preparation of 3 , as compared with previously reported syntheses.