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Further studies on the reaction of N ‐(2‐Hydroxyphenyl)anthranilic acids with acetic anhydride
Author(s) -
Kim Dong Han
Publication year - 1981
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.5570180722
Subject(s) - acetic anhydride , chemistry , anthranilic acid , acetic acid , organic chemistry , hydrazine (antidepressant) , reaction conditions , pummerer rearrangement , medicinal chemistry , catalysis , chromatography
Reaction of N ‐(2‐hydroxyphenyi)anthranilic acids (I) with acetic anhydride was investigated further. Treatment of Ia with refluxing acetic anhydride for 3 hours afforded two minor products, IIIa and IV, in addition to the previously reported IIa. Under similar conditions, the reaction of Ib with acetic anhydride afforded IIb as reported previously, and IIIb and IXb in small quantities. Treatment of IIIb with hydrazine gave X, and treatment of IXb with methoxyethylamine gave XI. When Ic was allowed to react with refluxing acetic anhydride, there were obtained three minor products, IIIc, IXc and XIII, in addition to IIc. Reaction of Id with acetic anhydride gave IId, and two minor products IXc and XIV. The formation of these minor products in the reaction of Ia‐d with acetic anhydride are discussed based on the reation mechanism proposed previously for the formation of II.