Methyl acetopyruvate → 1-benzyl-5-methyl-1h-pyrazole-3-carboxylate

HRID 2400542

Reaktionsgleichung

Reaktionsgleichung von HRID 2400542
[CH3:1][C:2]([CH2:4][C:5]([C:7]([O:9]C)=[O:8])=O)=O.Cl.Cl.[CH2:13]([NH:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[CH3:1][C:2]1[N:20]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:21]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=1

Komponenten

4

Edukt 2

HCID 88600Methyl acetopyruvateHCID 146540Benzylhydrazine dihydrochloride

Produkt 1

HCID 103760031-benzyl-5-methyl-1h-pyrazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of methyl acetopyruvate (1.0 g, 6.94 mmol) and benzylhydrazine dihydrochloride (1.49 g, 7.63 mmol) in acetic acid (7 mL) was stirred for 4 h at 90° C. After removal of the solvent (rotavapor), the residue was subjected to MPLC (silica, cyclohexane/ethyl acetate 10:1→2:1, followed by dichloromethane/methanol 10:1). The eluate obtained with dichloromethane/methanol contained the title compound as a crude product. After evaporation of the solvent, this fraction was further purified by preparative HPLC to afford the title compound (260 mg, 17%): 1H NMR (400 MHz, DMSO-d6) δ 12.57 (s, 1H), 7.37-7.27 (m, 3H), 7.12 (d, 2H), 6.53 (s, 1H), 5.36 (s, 2H), 2.22 (s, 3H).

Aufarbeitung

  1. customAfter removal of the solvent (rotavapor)
  2. customThe eluate obtained with dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-d5b6d9690a2d416aa4211e948914fca9
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796253B2

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