3-Acetylpyridine → HCID 67824059, compound

HRID 1197807Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][C:4]([C:6]([OH:8])=[O:7])=O.[C:9]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])[CH3:10]>>[O:11]=[C:9]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:10]/[C:4](=[CH:3]\[CH2:2][CH3:1])/[C:6]([OH:8])=[O:7]

Participants

Reactant 2

HCID 95893-Acetylpyridine

HCID 745632-Oxovaleric acid

Product 1

HCID 67824059HCID 67824059, compound

Procedure

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)+.

Sources & evidence

ORD record: ord-31d4645b44a64aa0b7bf18935f28f509
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05278161

Reaction notes

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