Phenylhydrazine → Ethyl 3-methyl-1-phenylpyrazole-5-carboxylate

HRID 1816620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816620
O=[C:2]([CH2:8][C:9](=O)[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)(=O)C>[CH3:10][C:9]1[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:19]=1.[CH3:10][C:9]1[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:19]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:8]=1

Komponenten

5

Edukt 2

HCID 7516PhenylhydrazineHCID 69208Ethyl 2,4-dioxovalerate

Produkt 2

HCID 2746772Ethyl 3-methyl-1-phenylpyrazole-5-carboxylateHCID 10900438Ethyl 5-methyl-1-phenyl-1H-pyrazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2 ml ethyl 2,4-dioxovalerate and 1.2 g phenyl hydrazine were dissolved in 20 ml acetic acid, followed by stirring at 100° C. for 2 hours. After evaporating acetic acid, ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography, to give 0.37 g of ethyl 3-methyl-1-phenyl-1H-5-pyrazolecarboxylate with hexane:ethyl acetate (14:1) and 0.46 g of ethyl 5-methyl-1-phenyl-1H-3-pyrazolecarboxylate with hexane:ethyl acetate (9:1).

Aufarbeitung

  1. customAfter evaporating acetic acid, ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f288b1ed3a0a4d9b8821f343cbfd88bf
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884821B1

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