Imidazo[1,5-a]pyridines in acetic acid solution are readily nitrated by nitric acid–sulphuric acid, although in some instances treatment of the base hydrogensulphate with nitric acid–acetic acid is preferred. Nitration occurs most readily in the 1-position, but 3-nitration occurs if the 1-position is already substituted.
E. E. Glover and L. W. Peck, J. Chem. Soc., Perkin Trans. 1, 1980, 959 DOI: 10.1039/P19800000959
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