1-(5-methoxycarbonyl-4-nitro-2-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic acid methyl ester → 1-(4-amino-5-methoxycarbonyl-2-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[C:13]([N+:20]([O-])=O)=[CH:12][C:11]=2[C:23]([F:26])([F:25])[F:24])[CH:9]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[C:13]([NH2:20])=[CH:12][C:11]=2[C:23]([F:25])([F:26])[F:24])[CH:9]=1)=[O:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1.1 g (2.95 mmoles) of 1-(5-methoxycarbonyl-4-nitro-2-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic acid methyl ester in 400 ml methanol is treated with 163 mg of 10% palladium on charcoal and hydrogenated at room temperature under a pressure of 5 bar for 18 hours. After filtration of the catalyst and evaporation of the solvent the residue is chromatographed on silica gel using dichlormethane and rising quantities of up to 15% of methanol. Recrystallization of the residue from dichloromethane and hexane gives 932 mg (2.715 mmol, 92%) of 1-(4-amino-5-methoxycarbonyl-2-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic acid methyl ester, m.p. 206 -208° C., ES-MS: m/z 344 [M+H]+.
Workup
- filtrationAfter filtration of the catalyst and evaporation of the solvent the residue
- customis chromatographed on silica gel
- customRecrystallization of the residue from dichloromethane and hexane
Sources & evidence
- ORD record
- ord-a0c2e9fdfc3d4721bc0253e6f99300bf
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299085B2
Reaction notes
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