Hydrazine hydrate (1:1) → 3-(3-chlorophenyl)-1H-pyrazol-5-amine

HRID 1452747

Reaktionsgleichung

Reaktionsgleichung von HRID 1452747
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.O.[NH2:14][NH2:15]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([NH2:11])[NH:14][N:15]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 1408553-(3-Chlorophenyl)-3-oxopropanenitrile

Produkt 1

HCID 1785072813-(3-chlorophenyl)-1H-pyrazol-5-amineAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirring solution of 3-(3-chlorophenyl)-3-oxo-propionitrile (2 g, 11.1 mmol) in absolute ethanol (20 mL) was added hydrazine hydrate (3.24 mL, 67 mmol). The reaction mixture was stirred at 80° C. for 15 h, cooled to room temperature, concentrated in vacuo, and absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2Cl2 as eluent provided 1.53 g (70%) of 5-(3-chloro-phenyl)-2H-pyrazol-3-ylamine as a green solid. 1H NMR (d6-DMSO) δ: 11.6 and 11.9 (2 broad s, 1H, NH+tautomer), 7.69 (s, 1H), 7.60 (d, 1H), 7.38 (t, 1H), 7.29 (d, 1H), 5.77 (broad s, 1H), 4.98 (broad s, 2H, NH2).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customabsorbed on silica gel
  4. customPurification on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-2d677c6526434529936ed8df86d12909
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473783B2

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