Tetrakis-(2-pyridyl)porphyrin (III) was prepared by condensation between pyridine-2-carboxaldehyde (I) and pyrrole (II) in refluxing propionic acid. Metallation of porphyrin (III) was performed with MnCl2, which spontaneously underwent oxidation, yielding the Mn3+ complex (IV). Subsequent N-alkylation of the pyridine rings with ethyl iodide produced the corresponding pyridinium iodide salt, which was transformed to the analogous chloride by treatment with tetrabutylammonium chloride (1). In an alternative procedure, initial quaternization of the pyridine rings of porphyrin (III) with ethyl p-toluenesulfonate afforded (V), which was further metallated with MnCl2 to give the title compound.