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

HRID 1636362Notes

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>>[CH3:19][C:17]1[CH2:16][C:15](=[O:14])[N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[N:2]=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 p-hydrazinobenzoic acid and ethylacetoacetate, 4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)-benzoic acid is obtained. Subsequent reaction with 2-(2-propenyloxy)aniline yields 4-(4,5-dihydro-3-methyl-5-oxo-4-(2-(2-propenyloxy)-anilinomethylene)-1H-pyrazol-1-yl)-benzoic acid, Mp 267.9° C.

Sources & evidence

ORD record: ord-f9d6607de9c24a69897556ed1840547b
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034099

Reaction notes

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