2-Aminophenols Containing Electron-Withdrawing
Groups from N-Aryl Hydroxylamines

Achim Porzelle; Anthony W. J. Cooper; Michael D. Woodrow; Nicholas C. O. Tomkinson

doi:10.1055/s-0030-1258546

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Synlett 2010(16): 2471-2473
DOI: 10.1055/s-0030-1258546

LETTER

2-Aminophenols Containing Electron-Withdrawing Groups from N-Aryl Hydroxylamines

Achim Porzelle^a, Anthony W. J. Cooper^b, Michael D. Woodrow^b, Nicholas C. O. Tomkinson*^a
^a School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK
e-Mail: tomkinsonnc@cardiff.ac.uk;
^b GlaxoSmithKline Medicines Research Centre, Stevenage, Hertfordshire, SG1 2NY, UK

Further Information

Publication History

Received 19 July 2010
Publication Date:
26 August 2010 (online)

Abstract
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Abstract

Reaction of substituted N-aryl hydroxylamines with methanesulfonyl chloride, p-toluenesulfonyl chloride, or trifluoromethanesulfonic anhydride under basic conditions leads to the rearranged 2-aminophenols (45-94%). The overall reaction sequence can be performed using polymer-supported sulfonyl chloride resin allowing for the effective conversion of N-aryl hydroxylamines to the 2-aminophenols without the need for chromatography.

Key words

rearrangement - hydroxylamine - solid-phase synthesis - 2-aminophenol

References and Notes

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All rearrangement products were characterised by ^¹H NMR, ^¹³C NMR, LRMS, and HRMS.