Ethyl Acetoacetate → 4-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

HRID 1636345Notes

Reaction equation

[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].C([O:14][C:15](=O)[CH2:16][C:17]([CH3:19])=O)C>>[O:14]=[C:15]1[N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[N:2]=[C:17]([CH3:19])[CH2:16]1

Participants

Reactant 2

HCID 8868Ethyl Acetoacetate

HCID 120894-Hydrazinobenzoic acid

Product 1

HCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Procedure

From the reaction of 4-hydrazinobenzoic acid and ethylacetoacetate, 4-(4,5-dihydro-5-oxo-3-methyl-1H-pyrazol-1-yl)-benzoic acid is obtained. Subsequent reaction with 2-ethylaniline yeilds 4-(4-(2-ethylanilinomethylene)-4,5-dihydro-5-oxo-3-methyl-1H-pyrazol-1-yl)-benzoic acid, Mp 291° C.

Sources & evidence

ORD record: ord-de879adfbac14f2b8e48d0ac2982885a
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034099

Reaction notes

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