Methanol → 4-[1-(3-Amino-pyrazol-1-yl)-butyl]-benzoic acid methyl ester

HRID 546102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546102
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:14]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[N:15]2)[CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1.CO.NN>C(OCC)(=O)C.[Ni].O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]([N:14]2[CH:18]=[CH:17][C:16]([NH2:19])=[N:15]2)[CH2:11][CH2:12][CH3:13])=[CH:8][CH:9]=1

Komponenten

7

Edukt 3

HCID 887MethanolHCID 9321HydrazineHCID 67188885HCID 67188885, Verbindung

Produkt 1

HCID 671891404-[1-(3-Amino-pyrazol-1-yl)-butyl]-benzoic acid methyl esterAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The 4-[1-(3-nitro-pyrazol-1-yl)-butyl]-benzoic acid methyl ester (127 mg, 0.42 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL) was added. While stirring, a 50% slurry of raney nickel in water (500 μL) was added followed by hydrazine (150 μL). Immediate effervescence was observed. The reaction continued to stir and bubble for 30 min. The reaction was passed through a plug of celite and concentrated in vacuo to afford 4-[1-(3-amino-pyrazol-1-yl)-butyl]-benzoic acid methyl ester (108 mg, 94%) as a clear oil: ESI-LRMS m/e calcd for C15H19N3O2 [M+] 273.15, found 274.29 [M+H+], 547.43 [2M+H+].

Aufarbeitung

  1. stirringto stir
  2. custombubble for 30 min
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c1aa66a301824c29b9cebee706986221
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935699B2

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