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

HRID 2069295Notes

Reaction equation

HRID 2069295 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]#[N:16])[N:12]=[CH:11]2)[C:7]([C:17]([F:20])([F:19])[F:18])=[CH:6][C:5]=1[N+:21]([O-])=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]#[N:16])[N:12]=[CH:11]2)[C:7]([C:17]([F:18])([F:19])[F:20])=[CH:6][C:5]=1[NH2:21]

Participants

4

Reactant 1

HCID 589644895-(4-Cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 589645122-Amino-5-(4-cyano-imidazol-1-yl)-4-trifluoromethyl-benzoic acid methyl esterYield 11%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 350 mg (1.03 mmoles) of 5-(4-cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester in 100 ml methanol is treated with 22 mg of 10% palladium on charcoal and hydrogenated at room temperature under a pressure of 1 bar for 16 hours. After filtration of the catalyst and evaporation of the solvent the residue is chromatographed on silica gel using dichloromethane and rising quantities of up to 15% of methanol to give 35 mg (0.113 mmol, 11%) of amorphous 2-amino-5-(4-cyano-imidazol-1-yl)-4-trifluoromethyl-benzoic acid methyl ester, ES-MS: m/z 311 [M+H]+.

Workup

  1. filtrationAfter filtration of the catalyst and evaporation of the solvent the residue
  2. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-30593d6c590945bfbfcefc1733dc2ab6
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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