Sodium Hydroxide → 2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

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Reaction Steps

248.2 g (0.96 mol) of 2-methyl-5-nitrophenylguanidine nitrate are added to a solution of 170 g (0.96 mol) of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one in 2.0 liters of isopropanol. After the addition of 42.5 g of sodium hydroxide, the reddish suspension is boiled at reflux for 12 hours. After cooling to 0°, filtration, washing with 2.0 liters of isopropanol and 3×400 ml of methanol and drying, there is obtained N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine, m.p. 195°-198°, Rf =0.68 (methylene chloride:methanol=9.1).

Provenance & Evidence