Phthalimide undergoes quantitative conversion into isoindolin-1-one (3c) upon hydrogenation in ethyl acetate over 10% palladium–carbon in the presence of trifluoroacetic acid, but resists reduction in its absence. This reaction is also promoted by iron(II) sulphate. The effect of N- and ring-substitution on the trifluoroacetic acid-promoted reduction has been investigated.
A. J. McAlees, R. McCrindle and D. W. Sneddon, J. Chem. Soc., Perkin Trans. 1, 1977, 2038 DOI: 10.1039/P19770002038
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