Hydrazine hydrate (1:1) → 3-(6-Hydrazinyl-3-pyridazinyl)benzonitrile

HRID 655240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655240
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:4][CH:3]=1.O.[NH2:17][NH2:18]>N1C=CC=CC=1>[NH:17]([C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:4][CH:3]=1)[NH2:18]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 135734663-(6-chloropyridazin-3-yl)benzonitrile

Produkt 1

HCID 593204453-(6-Hydrazinyl-3-pyridazinyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of 3-(6-chloro-pyridazin-3-yl)-benzonitrile (75.6 g, 350 mmol) in 900 mL of dried pyridine was cooled in an ice bath and 119.2 mL of hydrazine hydrate was added. The cooling was continued so as to keep the temperature below 30° C. at which time yellow needle separated. The mixture was then heated to 65° C. and stirred overnight. Then the mixture was concentrated and the residue was washed with water and Methanol to return the title compound (60 g, 81%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 8.38˜8.39 (m, 1H), 8.32˜8.35 (m, 1H), 8.24 (s, 1H), 7.97˜8.00 (d, 1H), 7.82˜7.85 (m, 1H), 7.64˜7.69 (m, 1H), 7.09˜7.12 (d, 1H), 4.39 (s, 2H); MS (m/z) 212.1 [M++1].

Aufarbeitung

  1. customthe temperature below 30° C.
  2. customseparated
  3. concentrationThen the mixture was concentrated
  4. washthe residue was washed with water and Methanol

Quellen und Nachweise

ORD-Eintrag
ord-73feae6e76744d418aaa1eb8fb44e955
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071581B2

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