Water → 3-Amino-5-nitroindazole

HRID 227694

Reaktionsgleichung

Reaktionsgleichung von HRID 227694
[OH2:1].[NH2:2][NH2:3].Cl[C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:6]=1[C:7]#[N:8].[OH2:16]>N1C=CC=CC=1>[N+:13]([C:10]1[CH:9]=[C:6]2[C:5](=[CH:12][CH:11]=1)[NH:3][N:2]=[C:7]2[NH2:8])([O-:16])=[O:1]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 855042-Chloro-5-nitrobenzonitrile

Produkt 1

HCID 31366553-Amino-5-nitroindazoleAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Hydrazine monohydrate (2.1 mL, 44 mmol) was added to a solution of 2-chloro-5-nitrobenzonitrile (7.30 g, 40 mmol) in pyridine (30 mL) and the mixture was heated to reflux overnight. The dark red solution was then cooled, poured into H2O and the resulting solid filtered and dried to give the title compound as a dark red powder (5.7 g, 80%). NMR 1H NMR (400 MHz, DMSO-D6) δ ppm 8.95 (d, J=2.0, 1H), 8.06 (dd, J=9.2, 2.0, 1H), 7.34 (d, J=9.2, 1H), 5.98 (br s, 2H) MS m/z 179.0 [M+H]+

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe dark red solution was then cooled
  4. filtrationthe resulting solid filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d4f7d523609746209c9ba165007cd546
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560467B2

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