Ethyl 2-acetylacetoacetate → 3,5-Dimethyl-1-(3-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1011931

Reaktionsgleichung

Reaktionsgleichung von HRID 1011931
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([NH:11][NH2:12])[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[CH3:13][CH2:14][O:15][C:16]([CH:18]([C:22]([CH3:24])=O)[C:19]([CH3:21])=O)=[O:17]>CC(O)=O.O>[CH2:14]([O:15][C:16]([C:18]1[C:19]([CH3:21])=[N:12][N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=2)[C:22]=1[CH3:24])=[O:17])[CH3:13]

Komponenten

5

Edukt 2

HCID 79063Ethyl 2-acetylacetoacetateHCID 54642853-Nitrophenylhydrazinium(1+) chloride

Produkt 1

HCID 6569693,5-Dimethyl-1-(3-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Following the procedure described in Helvetica Chimica Acta (1952), 35, 478-85, 5.00 g (26.37 mmmol) of 3-nitrophenylhydrazine hydrochloride suspended in 46 ml of 55% aqueous AcOH were dissolved by careful heating and treated (without further heating) with 4.13 ml (26.37 mmol) of ethyl diacetoacetate. The reaction was immediately cooled and kept 20 h at 0° C. The precipitate was diluted with 28 ml of water and after 6 h filtered and washed with 2×5 ml of water to give after drying under reduced pressure 4.66 g (61%) of the title compound as a light yellow solid. MS: 289.9 (MH+).

Aufarbeitung

  1. dissolutionwere dissolved
  2. temperatureby careful heating
  3. additiontreated
  4. temperatureThe reaction was immediately cooled
  5. filtrationfiltered
  6. washwashed with 2×5 ml of water
  7. customto give
  8. dry with materialafter drying under reduced pressure 4.66 g (61%) of the title compound as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-371089480d91497fa306dbb83d9dedc1
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977358B2

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