Nitric Acid → 2,3-Dimethyl-8-(2,6-dimethylbenzylamino)-7-nitroimidazo[1,2-a]pyridine
Reaktionsgleichung
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][CH:7]=[CH:6][N:5]2[C:20]=1[CH3:21].[N+:22]([O-])([OH:24])=[O:23]>C(O)(=O)C>[CH3:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:20]([CH3:21])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[CH:7][C:8]=1[N+:22]([O-:24])=[O:23]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 82.5 °C
Versuchsvorschrift
2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine (2.0 g, 7.16 mmol) was dissolved in acetic acid (30 ml) and nitric acid (0.53 g, 7.57 mmol) was added. The mixture was heated to 80-85° C. and stirred for 3 h at this temperature. After evaporation of the major part of the acetic acid, the residue was partitioned between methylene chloride and water. The organic layer was washed with a solution of sodium carbonate and the solvent was removed under reduced pressure. The residue was dissolved in methylene chloride (100 ml) and filtered through silica gel (10 g) whereupon the methylene chloride was removed under reduced pressure. Chromatography with methylene chloride (100%) gave 0.4 g (17%) of the title compound.
Aufarbeitung
- customAfter evaporation of the major part of the acetic acid
- customthe residue was partitioned between methylene chloride and water
- washThe organic layer was washed with a solution of sodium carbonate
- customthe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in methylene chloride (100 ml)
- filtrationfiltered through silica gel (10 g) whereupon the methylene chloride
- customwas removed under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-be32d2f5a7e84ed1bcc61181cb3526d5
- Quelldatensatz
- uspto-grants-2003_06
- Patentnummer
- US06579884B1
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