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Synthesis of 4‐vinylquinoline: Pyrolytic rearrangement of the 4‐(1‐hydroxyethyl)quinoline and related derivatives
Author(s) -
Rodriguez J. G.,
Benito Y.
Publication year - 1988
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.5570250323
Subject(s) - chemistry , quinoline , yield (engineering) , ylide , wittig reaction , xanthate , derivative (finance) , sodium hydroxide , ethanol , organic chemistry , medicinal chemistry , pyrolytic carbon , dehydration , dimethyl sulfate , pyrolysis , economics , financial economics , metallurgy , biochemistry , materials science
The synthesis of 4‐vinylquinoline has been carried out by means of the Wittig reaction between 4‐quino‐linecarbaldehyde and the methyl triphenylphosphonium ylide in dimethyl sulphoxide in good yield. Dehydration of the 4‐(1‐hydroxyethyl)quinoline and their xanthate derivative, give equimolar amounts of 4‐ethylquinoline and 4‐acetylquinoline while small amounts of 4‐vinylquinoline were found. Dehydrochlorination of 4‐(1‐chloroethyl)quinoline in ethanol‐sodium hydroxide provides 4‐ethyl‐3‐ethoxyquinoline in good yield, but 4‐vinylquinoline is a minor reaction product.