HCID 53916534, compound → HCID 19853671, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9](=[O:16])[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[O:13]>O1CCOCC1.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 9.342 g (41.854 mM) of methyl 4-(2-amino-5-fluorophenyl)-4-oxo-2-butenoate in 200 ml of dioxane is hydrogenated in the presence of 10% of Pd-C at room temperature under atmospheric pressure. The reaction mixture is concentrated after removal of the catalyst. The resulting residue is chromatographed on a column of silica gel (463 g), eluting with toluene-ethyl acetate (19:1 v/v) to give 8.47 g of methyl 4-(2-amino-5-fluorophenyl)-4-oxobutyrate as orange crystals. Recrystallization from CH2Cl2 -Et2O-n-hexane gives 7.615 g (Yield: 80.8%) of the objective compound melting at 102°-103° C. as white needles.