Benzoylacetonitrile → 1-(2-methylphenyl)-3-phenyl-1H-pyrazol-5-amine

HRID 63247

Reaktionsgleichung

Reaktionsgleichung von HRID 63247
[C:1]([CH2:9][C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:13]1([CH3:21])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][NH2:20]>CO>[C:2]1([C:1]2[CH:9]=[C:10]([NH2:11])[N:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH3:21])[N:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 64799BenzoylacetonitrileHCID 71554o-Tolylhydrazinium(1+) chloride

Produkt 1

HCID 120499741-(2-methylphenyl)-3-phenyl-1H-pyrazol-5-amineAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Benzoylacetonitrile (500 mg, 3.44 mmol) and o-tolylhydrazine hydrochloride (574 mg, 3.61 mmol) were placed in a microwave vial and dissolved in methanol (1.7 mL). The reaction vessel was sealed, placed in a microwave oven and heated at 120° C. for 1 hour. After this period, the reaction mixture was concentrated onto silica gel and purified by flash chromatography (0-50% ethyl acetate/hexanes gradient) to afford the desired intermediate, 5-phenyl-2-o-tolyl-2H-pyrazol-3-ylamine (392 mg). LC/MS: Calc. C16H15N3 249.13 amu; Obs. [M+H]+=250.2 amu.

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. customplaced in a microwave oven
  3. waitAfter this period
  4. concentrationthe reaction mixture was concentrated onto silica gel
  5. custompurified by flash chromatography (0-50% ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-463d2c9fe0064459b0b0a809e8778bb7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447058B2

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