Ethyl Acetoacetate → 2,4-dihydro-5-methyl-2-(2-pyridinyl)-3H-Pyrazol-3-one

HRID 1636347Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][NH2:8].C([O:11][C:12](=O)[CH2:13][C:14]([CH3:16])=O)C>>[CH3:16][C:14]1[CH2:13][C:12](=[O:11])[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:8]=1

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 786452-Hydrazinopyridine

Product 1

HCID 6676522,4-dihydro-5-methyl-2-(2-pyridinyl)-3H-Pyrazol-3-one

Procedure

From the reaction of 2-pyridylhydrazine and ethylacetoacetate, 2,4-dihydro-5-methyl-2-(2-pyridyl)-3H-pyrazol-3-one is obtained. Subsequent reaction with 2-ethylaniline yields 4-(2-ethylanilinomethylene)-2,4-dihydro-5-methyl-2-(2-pyridyl)-3H-pyrazol-3-one, Mp 182.9° C.

Sources & evidence

ORD record: ord-70a3586652d64a4b922395fd5e505443
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034099

Reaction notes

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