2-(4-Fluoro-5-nitrobenzoyl)-3-methylpyridine → 3-Amino-4-fluorophenyl 3-methyl-2-pyridyl ketone
Reaction equation
[F:1][C:2]1[C:16]([N+:17]([O-])=O)=[CH:15][C:5]([C:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1>[Fe].C(O)(=O)C>[CH3:14][C:13]1[C:8]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[C:16]([NH2:17])[CH:15]=2)=[O:7])=[N:9][CH:10]=[CH:11][CH:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of 2-(4-fluoro-5-nitrobenzoyl)-3-methylpyridine (7.13 g, 0.0258 mol) and glacial acetic acid at 70-80° C. is added iron powder (7.76 g, 0.130 mol) in three portions. The resultant mixture is stirred overnight at 70-80° C., cooled to room temperature and extracted three times with ethyl acetate. The combined organic layers are filtered through Celite, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title compound as a tan solid (4.36 g, 69.8%) which is identified by NMR spectral analysis.