2-(2-Chloro-4-fluorophenyl)-3-methyl-5-nitropyridine → 6-(2-Chloro-4-fluorophenyl)-5-methylpyridin-3-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][N:10]=1>[Ni].CO.CO>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[CH:11][C:12]([NH2:16])=[CH:13][C:14]=1[CH3:15]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A 250 mL round bottom flask was charged with 2-(2-chloro-4-fluorophenyl)-3-methyl-5-nitropyridine (4 g) and methanol (50 mL). To the flask was added Raney nickel/methanol slurry (approx 4 g). The flask was evacuated and charged with hydrogen several times. The mixture was stirred under a balloon of hydrogen for 2.5 h. The flask was purged with nitrogen. The catalyst was filtered off and the filtrate was concentrated under reduced pressure giving 6-(2-chloro-4-fluorophenyl)-5-methylpyridin-3-amine as an off white solid. Mass spectrum (EST) 237 (M+1).