Ethyl 4-azido-2-fluoro-3-methylbenzoate → Ethyl 4-amino-2-fluoro-3-methylbenzoate
Reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:15])[C:5]=1[CH3:16])=[N+]=[N-]>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:15])[C:5]=1[CH3:16]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In 40 ml of ethanol was dissolved 2.00 g of ethyl 4-azido-2-fluoro-3-methylbenzoate, followed by adding thereto 0.40 g of 5% palladium-carbon, and the resulting mixture was stirred at room temperature for 5 hours under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a column chromatography (eluent; toluene:ethyl acetate=10:1) to obtain 0.75 g of ethyl 4-amino-2-fluoro-3-methylbenzoate as colorless crystals.