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A new ring opening reaction of N ‐aminophthalimide hydrazones
Author(s) -
Hearn Michael J.,
Rosenberg Judith,
Campbell Mary L.
Publication year - 1985
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.5570220556
Subject(s) - chemistry , moiety , hydrazine (antidepressant) , ring (chemistry) , aqueous solution , phthalic acid , organic chemistry , phthalic anhydride , sodium salt , hydrazone , base (topology) , medicinal chemistry , polymer chemistry , inorganic chemistry , chromatography , catalysis , mathematical analysis , mathematics
Araldehyde hydrazones III of N ‐aminophthalimide underwent rapid ring opening reactions initiated by the addition of excess base to their refluxing methanolic solutions. The products were conveniently isolated through liquid‐liquid extraction as the stable sodium salts V, and acidification precipitated the resulting phthalic acid congeners VI from aqueous solution. Compounds III readily exchanged one hydrazine moiety for another. For example, IIId reacted with 2,4‐dinitrophenylhydrazine to give the 2,4‐dinitrophenylhydrazone of 4‐chlorobenzaldehyde (VIId, 93%). Nonetheless, IIIg reacted exclusively at the carboxaldehyde function to give products VIIIa and VIIIb.