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On the bromination of 1,7‐ and 1,8‐Naphthyridine in nitrobenzene
Author(s) -
Van Der Plas H. C.,
Wozniak M.
Publication year - 1976
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.5570130505
Subject(s) - bromine , halogenation , chemistry , hydrobromide , nitrobenzene , bromide , yield (engineering) , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
By application of the Kress procedure for bromination it has been found that from the hydro‐bromide of 1,7‐naphthyridine with 1.1 equivalents of bromine in nitrobenzene a mixture of 3‐and 5‐bromo‐ and 3,5‐dibromo‐1,7‐naphthyridine is obtained in reasonable yield. With an excess of bromine 3,5‐dibromo‐1,7‐naphthyridine is nearly exclusively formed. Similar brominations of the hydrobromide of 1,8‐naphthyridine with 1.1 equivalents of bromine gave 3‐bromo‐ and 3,6‐dibromo‐1,8‐naphthyridine. By using an excess of bromine a high‐yield conversion into 3,6‐dibromo‐1,8‐naphthyridine is observed. Bromination of the hydrochloride salt of 1,7‐ and 1,8‐naphthyridine affords the same bromo derivatives.