2,4-Dimethyl-5-nitroaniline → 5-methyl-6-nitro-1H-indazole
Reaktionsgleichung
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH2:4].[N:13]([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:9][C:7]1[CH:8]=[C:2]2[C:3](=[CH:5][C:6]=1[N+:10]([O-:12])=[O:11])[NH:4][N:13]=[CH:1]2Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
2,4-Dimethyl-5-nitroaniline (1.662 g, 10.00 mmol) was dissolved in glacial acetic acid (100 ml) and the mixture was cooled to 0° C. A solution of sodium nitrite (1 eq, 690 mg) in water (2 ml) was added while maintaining a temperature below 25° C. Stirring was continued for three hours and the mixture was filtered. The filtrate was allowed to stand for three days at room temperature, then was concentrate under reduced pressure. The residue was diluted with water and the resulting mixture was stirred vigorously. The solid product was collected by filtration, washed thoroughly with cold water, and dried. The product was purified by flash chromatography (99:1 dichloromethane/methanol) to give 1.030 g (58.1%) of 5-methyl-6-nitro-1H-indazole as a solid.
Aufarbeitung
- temperaturewhile maintaining a temperature below 25° C
- filtrationthe mixture was filtered
- waitto stand for three days at room temperature
- concentrationwas concentrate under reduced pressure
- additionThe residue was diluted with water
- stirringthe resulting mixture was stirred vigorously
- filtrationThe solid product was collected by filtration
- washwashed thoroughly with cold water
- customdried
- customThe product was purified by flash chromatography (99:1 dichloromethane/methanol)
Quellen und Nachweise
- ORD-Eintrag
- ord-34ca48c223cf48389784a9d964907b2c
- Quelldatensatz
- uspto-grants-2014_10
- Patentnummer
- US08871760B2
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