Abstract Two general procedures involving the condensation of phthalonitrile or 1, 3- diiminoisoindoline with various aminopicolines, followed by ring expansion with hydrazine to the corresponding phthalazine are described. Syntheses are reported of 1, 4-di (3′- methyl-2′-pyridyl) aminophthalazine, 1, 4-di (5′-methyl-2′-pyridyl) aminophthalazine, and 1, 4-di (4′, 6′-dimethyl-2′-pyridyl) aminophthalazine.