Hydrazine → 4,5-Diphenyl-1,2-dihydropyrazol-3-one

HRID 1838626

Reaktionsgleichung

Reaktionsgleichung von HRID 1838626
C([O:3][C:4](=O)[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.C(O)(=O)C1(CCC(C(O)=O)C1(C)C)C.[NH2:35][NH2:36]>C(O)C>[C:14]1([C:5]2[C:4](=[O:3])[NH:35][NH:36][C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 9321HydrazineHCID 214911,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acidHCID 11010997Ethyl beta-oxo-alpha-phenylbenzenepropanoate

Produkt 1

HCID 2560164,5-Diphenyl-1,2-dihydropyrazol-3-oneAusbeute 32,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 20 mL of an ethanol solution of 1.2 g (4.47mmol) of 3-oxo-2,3-diphenylpropionic acid ethyl ester was added 1.04 g (4.47 mmol) of camphoric acid and 140 μL(4.47 mmol) of hydrazine. After the mixture was refluxed for 20 min, the solvent was removed in vacuo, and the residue was triturated with 40% ethyl acetate/hexane (2 mL) three times to afford 343 mg of 4,5-diphenyl-1,2-dihydropyrazol-3-one in 27% yield.

Aufarbeitung

  1. temperatureAfter the mixture was refluxed for 20 min
  2. customthe solvent was removed in vacuo
  3. customthe residue was triturated with 40% ethyl acetate/hexane (2 mL) three times

Quellen und Nachweise

ORD-Eintrag
ord-a7b335d6ba3d4ef285211df8f3ab7ccf
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673923B2

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