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The chemistry of 2 H ‐3,1‐benzoxazine‐2,4(1 H )‐dione (Isatoic Anhydride). 19 . Direct formation of 2‐aminobenzyl alcohols from the reduction of N ‐substituted isatoic anhydrides
Author(s) -
Coppola Gary M.
Publication year - 1986
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.5570230145
Subject(s) - chemistry , sodium borohydride , yield (engineering) , alcohol , benzyl alcohol , catalysis , nitro , organic chemistry , medicinal chemistry , catalytic hydrogenation , sodium , materials science , alkyl , metallurgy
Isatoic anhydrides 1 are easily reduced with sodium borohydride to o ‐(substituted‐amino)benzyl alcohols 3 in good yield. Sequential reduction of N ‐(2‐nitrobenzyl)isatoic anhydride ( 5 ) with sodium borohydride followed by catalytic hydrogenation of the nitro group affords the naturally occurring 2‐(2′‐aminobenzylamino)‐benzyl alcohol ( 4 ) in 72% yield.