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

HRID 2069297Notes

Reaction equation

HRID 2069297 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([Br:15])[N:12]=[CH:11]2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[N+:20]([O-])=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([Br:15])[N:12]=[CH:11]2)[C:7]([C:16]([F:19])([F:17])[F:18])=[CH:6][C:5]=1[NH2:20]

Participants

4

Reactant 1

HCID 693375825-(4-Bromo-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 589644952-Amino-5-(4-bromo-imidazol-1-yl)-4-trifluoromethyl-benzoic acid methyl esterYield 58.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a similar way a solution of 5-(4-bromo-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (300 mg, 0.8 mmol) in 50 ml methanol is hydrogenated over 43 mg of 10% palladium on charcoal to obtain after the usual workup procedure 160 mg (0.466 mmol, 58%) of 2-amino-5-(4-bromo-imidazol-1-yl)-4-trifluoromethyl-benzoic acid methyl ester, m.p. 163-165° C., ES-MS: m/z 365 [M+H]+.

Sources & evidence

ORD record
ord-76542aba986f43ac8b41b639af576a9c
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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