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The conversion of phenols to primary and secondary aromatic amines via a Smiles rearrangement

✍ Scribed by Coutts, Ian G. C.; Southcott, Mark R.


Book ID
118182327
Publisher
Royal Society of Chemistry
Year
1990
Weight
621 KB
Volume
3
Category
Article
ISSN
1472-7781

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8-Hydroxyquinoline (9) was converted to 8-aminequinoline (10) in a one-pot procedure involving alkylation with 2-bromo-2-methylpropionamide (2) followed by Smiles rearrangement and hydrolysis, in \(41 \%\) yield. The scope and limitations of this new procedure were explored with additional hydroxyqu