5-(4-Trifluoromethyl-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester → 2-Amino-5-(4-trifluoromethyl-imidazol-1-yl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069299Notes

Reaction equation

HRID 2069299 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[CH:11]2)[C:7]([C:19]([F:22])([F:21])[F:20])=[CH:6][C:5]=1[N+:23]([O-])=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[N:12]=[CH:11]2)[C:7]([C:19]([F:20])([F:21])[F:22])=[CH:6][C:5]=1[NH2:23]

Participants

4

Reactant 1

HCID 866148585-(4-Trifluoromethyl-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 589644732-Amino-5-(4-trifluoromethyl-imidazol-1-yl)-4-trifluoromethyl-benzoic acid methyl esterYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a similar way a solution of 5-(4-trifluoromethyl-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (1.0 g, 2.6 mmol) in 100 ml methanol is hydrogenated over 55 mg of 10% palladium on charcoal to obtain after the usual workup procedure 840 mg (2.38 mmol, 91%) of amorphous 2-amino-5-(4-trifluoromethyl-imidazol-1 -yl)-4-trifluoromethyl-benzoic acid methyl ester, ES-MS: m/z 354 [M+H]+.

Sources & evidence

ORD record
ord-786a20eeeb2542f7ac9ad81df67f32b3
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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