Methyl 4-fluoro-2-methyl-3-nitrobenzoate → Methyl 3-amino-4-fluoro-2-methylbenzoate
Reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-])=O>CO.[C].[Pd]>[NH2:13][C:3]1[C:4]([CH3:12])=[C:5]([CH:10]=[CH:11][C:2]=1[F:1])[C:6]([O:8][CH3:9])=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of a crudely purified product (6.00 g, purity 50%) of methyl 4-fluoro-2-methyl-3-nitrobenzoate and wet palladium carbon (10 wt %, 300 mg, 2.81 mmol) in methanol (100 mL) was stirred under hydrogen atmosphere for 4 hr. The catalyst was filtered off through celite, the filtrate was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/20→1/10) to give the title compound (2.13 g, yield 42%).