Hydrazine hydrate (1:1) → 3-Methoxy-4-nitrobenzohydrazide

HRID 419334

Reaktionsgleichung

Reaktionsgleichung von HRID 419334
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6](OC)=[O:7].O.[NH2:17][NH2:18]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([NH:17][NH2:18])=[O:7]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Produkt 1

HCID 218838753-Methoxy-4-nitrobenzohydrazideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To methyl 3-methoxy-4-nitrobenzoate (5.16 g, 24.5 mmol) in EtOH (250 mL) was added hydrazine monohydrate (5.95 mL, 122 mmol) in one portion. The reaction was heated at 80° C. overnight and concentrated upon completion by TLC. The residue was taken up in EtOAc, heated and hot filtered. The filtrate was concentrated and the residue was triturated with diethyl ether to provide the title compound (3.65 g, 17.3 mmol, 71%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.96 (s, 3H), 4.60 (br. s., 2H), 7.50 (dd, J=8.4, 1.5 Hz, 1H), 7.69 (d, J=1.8 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 10.05 (br. s., 1H).

Aufarbeitung

  1. concentrationconcentrated upon completion by TLC
  2. temperatureheated
  3. concentrationThe filtrate was concentrated
  4. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8caec853cd82465a9d01bdaf8f8adf24
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

Verknüpfte Notizen

Wird geladen…