Ammonium → 4-Chloro-5-nitropyridin-2-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH4+:11].[Mn]([O-])(=O)(=O)=O.[K+]>>[Cl:1][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[CH:4][N:5]=[C:6]([NH2:11])[CH:7]=1Participants
4
Conditions
- Temperature
- -33 °C
Procedure
To 4-chloro-3-nitropyridine (10.0 g, 63.1 mmol) in 500 ml of liquid ammonium was added potassium permanganate (19.9 g, 126.1 mmol). The reaction was stirred at this temperature (−33° C.) for 5 hours then slowly warmed to room temperature. After evaporation of ammonia, water (1 L) was added. The solid formed was collected by filtration and washed with water (2 L). The solid was extracted with 1:1=DCM:EtOAc (5×500 ml). The solvent was removed and the resulting solid was recrystallized from EtOAc (400 ml) to give the title compound as a yellow solid (4.4 g, 33%). 1H NMR (400 MHz) 8.88 (s, 1H), 7.65 (b, 2H), 6.62 (s, 1H).