3-Acetylpyridine → HCID 67824059, compound

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Reaction Steps

In a manner analogous to that described above, by an aldol condensation of 2-oxo-n-valeric acid with 3-acetylpyridine there is obtained γ-oxo-α-[(E)-propylidene]-3-pyridinebutyric acid, MS: 219 (M+H)+. Ring closure with hydrazine yields 4-propyl-6-(3-pyridyl)-3(2H)-pyridazinone, MS: 215 (M)+, which is converted into the corresponding chloride, 3-chloro-4-propyl-6-(3-pyridyl)pyridazine, MS: 233 (M)+. Hydrazinolysis to 3-hydrazino-4-propyl-6-(3-pyridyl)pyridazine, MS: 229 (M)+, and condensation with diethyl (3-pyridyl)malonate yields ethyl rac-8-propyl-α-(3-pyridylmethyl)-6-(3-pyridyl)-s-triazolo[4,3-b]pyridazine-3-acetate, which is converted by basic saponification into the above acid, MS: 388 (M)+.

Provenance & Evidence