Diethyl Malonate → HCID 19104906, compound

HRID 1197800Notes

Reaction equation

HRID 1197800 reaction equation
N(C1N=NC(C2C=CC=CC=2)=CC=1CCC)N.C(OCC)(=O)CC(OCC)=O.[C:29]1([C:35]2[CH:36]=[C:37]([CH2:50][CH2:51][CH3:52])[C:38]3[N:39]([C:41]([CH2:44][C:45]([O:47]CC)=[O:46])=[N:42][N:43]=3)[N:40]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[C:29]1([C:35]2[CH:36]=[C:37]([CH2:50][CH2:51][CH3:52])[C:38]3[N:39]([C:41]([CH2:44][C:45]([OH:47])=[O:46])=[N:42][N:43]=3)[N:40]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 19104933HCID 19104933, compoundHCID 19104966HCID 19104966, compound

Product 1

HCID 19104906HCID 19104906, compound

Procedure

In a manner analogous to Example 1, by chlorinating 6-phenyl-4-propyl-3(2H)-pyridazinone [Chim. Ther. 6, 109 (1971)] there is obtained 3-chloro-6-phenyl-4-propylpyridazine, MS: 232 (M)+, which is converted by hydrazinolysis into 3-hydrazino-6-phenyl-4-propylpyridazine, MS: 228 (M)+. Subsequent ring condensation with diethyl malonate to ethyl 6-phenyl-8-propyl-s-triazolo[4,3-b]pyridazine-3-acetate, MS: 324 (M)+, followed by basic saponification gives the above acid as a solid, MS: 252 (M-CO2)+.

Sources & evidence

ORD record
ord-bc46ff81396e475496fbc2f86aa94451
Source dataset
uspto-grants-1994_01
Patent number
US05278161

Reaction notes

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