HCID 21105743, compound → HCID 21105741, compound

HRID 1354471Notes

Reaction equation

HRID 1354471 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[N:16][N:17]=1)[C:7]([OH:9])=[O:8])([O-])=O>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[N:16][N:17]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 21105743HCID 21105743, compound

Product 1

HCID 21105741HCID 21105741, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-nitro-4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (0.600 g), 5% palladium on carbon (0.600 g) and tetrahydrofuran (15 ml) was stirred under a hydrogen atmosphere at room temperature and normal pressure for 30 min. Palladium on carbon was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1, volume ratio) to give 3-amino-4-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (0.33 g, yield 59%). Recrystallization from hexane-tetrahydrofuran gave yellow prism crystals. melting point: >300° C.

Workup

  1. filtrationPalladium on carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1, volume ratio)

Sources & evidence

ORD record
ord-e7fe12ec1b02467e83c72250ecdb6a0d
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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