4-Chlorophenylhydrazine sulfate → 2-[1-(4-chlorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]acetic acid

HRID 615006Notes

Reaction equation

[C:1]([CH:4]([C:9](=O)[CH3:10])[CH2:5][C:6]([OH:8])=[O:7])(=O)[CH3:2].[CH:12]1[C:17]([NH:18][NH2:19])=[CH:16][CH:15]=[C:14]([Cl:20])[CH:13]=1.OS(O)(=O)=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:2][C:1]1[C:4]([CH2:5][C:6]([OH:8])=[O:7])=[C:9]([CH3:10])[N:18]([C:17]2[CH:16]=[CH:15][C:14]([Cl:20])=[CH:13][CH:12]=2)[N:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4.0 grams 3,3-diacetyl-propionic acid, 4.9 grams p-chlorophenylhydrazine-sulfate, 2.1 grams anhydrous sodium acetate and 30 milliliters glacial acetic acid were mixed and the mixture was heated to 60° C. for 3 hours. The reaction mixture was evaporated and water was added to the residue. The precipitate formed thereby was separated by filtration and recrystallized from a mixture of ethanol and of water. 5.5 grams 3,5-dimethyl-1-(p-chlorophenyl)-pyrazol-4-acetic acid, melting at 176°-177° C., were obtained, representing a yield of 82%.

Workup

customThe reaction mixture was evaporated
additionwater was added to the residue
customThe precipitate formed
customthereby was separated by filtration
customrecrystallized from a mixture of ethanol and of water

Sources & evidence

ORD record: ord-85c8bcc668174d689adaae1b3411f4d9
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146721

Reaction notes

Loading…