Ethyl Acetoacetate → Ethyl 5-methyl-1-phenyl-1H-pyrazole-4-carboxylate

HRID 240805

Reaktionsgleichung

Reaktionsgleichung von HRID 240805
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH3:10]OC(OC)N(C)C.Cl.[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH3:5][C:3]1[N:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]=[CH:10][C:2]=1[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

5

Edukt 3

HCID 8868Ethyl AcetoacetateHCID 60962Phenylhydrazine hydrochlorideHCID 78373Dimethylformamide dimethyl acetal

Produkt 1

HCID 96680Ethyl 5-methyl-1-phenyl-1H-pyrazole-4-carboxylateAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of ethyl acetoacetate (1.5 g, 11.5 mmol) and dimethylformamide dimethyl acetal (1.68 mL, 12.7 mmol) was stirred at 120° C. for 2 hours. The reaction solution was cooled to room temperature, and a solution of phenyl hydrazine hydrochloride (1.67 g, 11.5 mmol) in ethanol (30 mL) was then added thereto. The obtained mixture was stirred at 80° C. for 2.5 hours. The reaction solution was cooled to room temperature, and it was then concentrated under reduced pressure. The residue was purified with a fractionation purification apparatus (Biotage, ethyl acetate:hexane=1:19-3:7), so as to obtain the title compound (2.32 g, 87%) in the form of a yellow oily product.

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringThe obtained mixture was stirred at 80° C. for 2.5 hours
  3. temperatureThe reaction solution was cooled to room temperature
  4. concentrationit was then concentrated under reduced pressure
  5. customThe residue was purified with a fractionation purification apparatus (Biotage, ethyl acetate:hexane=1:19-3:7)

Quellen und Nachweise

ORD-Eintrag
ord-56649bbc9a974d688e5688716682c800
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648103B2

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