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On the chichibabin amination of quinoline and some nitroquinolines
Author(s) -
Tondys Hanna,
van der Plas Henk C.,
Woźniak Marian
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.5570220226
Subject(s) - chemistry , potassium permanganate , quinoline , amination , liquid ammonia , amide , reagent , potassium , ammonia , electrophilic amination , organic chemistry , medicinal chemistry , catalysis
Quinoline is aminated into 2‐aminoquinoline (55‐60%) when treated with potassium amide/liquid ammonia/potassium permanganate at −65°. When the amination is carried out by allowing the solution of quinoline in potassium amide/liquid ammonia to raise from −60° to + 15° before addition of potassium permanganate, the main product is 4‐aminoquinoline. Using as reagent liquid ammonia/potassium permanganate (thus without the presence of potassium amide) 3‐nitroquinoline is exclusively aminated at −40° into 4‐amino‐3‐nitroquinoline. Using the same conditions, from 4‐nitroquinoline 3‐amino‐4‐nitroquinoline is obtained. The mechanism of these amination reactions is discussed.