Hydrazine hydrate (1:1) → 4-Cyanobenzohydrazide

HRID 470769

Reaktionsgleichung

Reaktionsgleichung von HRID 470769
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7](OCC)=[O:8])=[CH:5][CH:4]=1)#[N:2].O.[NH2:15][NH2:16]>C(O)C>[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([NH:15][NH2:16])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 81589Ethyl 4-cyanobenzoate

Produkt 1

HCID 4567324-CyanobenzohydrazideAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 250 mL round bottom flask charged with ethyl 4-cyanobenzoate (16.85 g, 96.2 mmol) in 95% ethanol (75 mL) was added hydrazine mono-hydrate (18.2 mL, 64% solution, 240 mmol). This mixture was heated to reflux for a period of 4.5 h, then allowed to cool to room temperature over a 16 h period. The solvent was removed under reduced pressure and the yellow residue was taken up in ice-cold water (150 mL). The light yellow solid was filtered off and washed with additional cold water (50 mL). The solid was then dried under high vacuum to yield the title compound as a light yellow solid (13.98 g, 90%). 1H NMR (400 MHz, DMSO-d6, δ in ppm) 10.05 (br s, 1H) 7.95 (AA′XX′, J=8.5 Hz, 4H), 4.61 (br s, 2H).

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureto reflux for a period of 4.5 h
  3. customThe solvent was removed under reduced pressure
  4. filtrationThe light yellow solid was filtered off
  5. washwashed with additional cold water (50 mL)
  6. customThe solid was then dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c33ed2630b134739b0597c89be6a8d38
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629167B2

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