Hydrazine hydrate (1:1) → 4-(1H-Pyrazol-1-yl)benzohydrazide

HRID 563289

Reaktionsgleichung

Reaktionsgleichung von HRID 563289
[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.O.[NH2:18][NH2:19]>CCO>[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([C:10]([NH:18][NH2:19])=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 973146Ethyl 4-(1H-pyrazol-1-YL)benzoate

Produkt 1

HCID 432366724-(1H-Pyrazol-1-yl)benzohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(1H-pyrazol-1-yl)benzoate (711 mg, 3.29 mmol) in absolute EtOH (50 mL) was added hydrazine monohydrate (1.6 mL, 32.9 mmol) at room temperature. The reaction mixture was heated to reflux and stirred for 6 d, then concentrated under reduced pressure. The residue was suspended in H2O (30 mL), filtered, washed with H2O (2×20 mL) and EtOH (2×20 mL) to provide the title compound as an off white solid (101 mg, 15%): 1H NMR (400 MHz, CDCl3, δ in ppm) 9.84 (s, 1H), 8.62-8.59 (m, 1H), 7.98-7.90 (m, 4H), 7.81-7.78 (m, 1H), 6.61-6.57 (m, 1H), 4.51 (br d, J=3.3 Hz, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. washwashed with H2O (2×20 mL) and EtOH (2×20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-83893b3eda2643acb87310bfcfcbf1a7
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067448B2

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