5-[4-(4-Methoxymethyl-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester → HCID 58964510, compound

HRID 2069282Notes

Reaction equation

HRID 2069282 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH3:23])=[CH:17][CH:16]=3)[N:12]=[CH:11]2)[C:7]([C:24]([F:27])([F:26])[F:25])=[CH:6][C:5]=1[N+:28]([O-])=[O:29]>O1CCCC1.[Pt]>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][O:22][CH3:23])=[CH:19][CH:20]=3)[N:12]=[CH:11]2)[C:7]([C:24]([F:25])([F:26])[F:27])=[CH:6][C:5]=1[NH:28][OH:29]

Participants

4

Reactant 1

HCID 589645075-[4-(4-Methoxymethyl-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 58964510HCID 58964510, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.00 g of 5-[4-(4-methoxymethyl-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester in 20 ml of tetrahydrofuran is hydrogenated in presence of 200 mg of platinum on carbon. After filtration of the catalyst the solution is evaporated to dryness yielding 0.661 g of 2-hydroxyamino-5-[4-(4-methoxymethyl-phenyl)-imidazol-1-yl]-4-trifluoromethyl-benzoic acid methyl ester as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): 3.30 s, 3H; 3.82 s, 3H; 4.40 s, 2H; 7.35 d, J=10.4 Hz, 2H; 7.62 s, 1H; 7.80 d, J=10.4 Hz, 2H; 7.85-7.90 m, 3H.

Workup

  1. filtrationAfter filtration of the catalyst the solution
  2. customis evaporated to dryness

Sources & evidence

ORD record
ord-7cf516a2fd8d45e1985e183c572f6151
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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