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Benzylhydrazine dihydrochloride → methyl 1-benzyl-3-methyl-1H-pyrazole-4-carboxylate

HRID 1488207
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1488207
CN(/[CH:4]=[C:5](/[C:10](=O)[CH3:11])\[C:6]([O:8][CH3:9])=[O:7])C.Cl.Cl.[CH2:15]([NH:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH2:15]([N:22]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:10]([CH3:11])=[N:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 146540Benzylhydrazine dihydrochlorideHCID 17874501Methyl 2-[(dimethylamino)methylene]acetoacetate

Produkt 1

HCID 66778578methyl 1-benzyl-3-methyl-1H-pyrazole-4-carboxylateAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (Z)-methyl 2-((dimethylamino)methylene)-3-oxobutanoate (15.8 g, 92.5 mmol) in ethanol (50 mL) was added 1-benzylhydrazine dihydrochloride (18 g, 92.3 mmol). The resulting solution was stirred for 3.5 h at 80° C., then concentrated under reduced pressure. The residue was dissolved in 200 mL of ethyl acetate. The organic layer was washed with 1×40 mL of water and 2×40 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:4) as the eluent to furnish 12.4 g (58%) of the title compound as a yellow solid.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 200 mL of ethyl acetate
  3. washThe organic layer was washed with 1×40 mL of water and 2×40 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:4) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-39f0383af1bf42949ccac08abbc295c5
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09428502B2

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