HCID 21105756, compound → HCID 21105740, compound

HRID 1354472Notes

Reaction equation

HRID 1354472 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=3[N+:25]([O-])=O)=[N:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].O1CCCC1>[NH2:25][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:16]=1[C:14]1[O:15][C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=2)=[N:12][N:13]=1)[C:20]([OH:22])=[O:21]

Participants

4

Reactant 1

HCID 21105756HCID 21105756, compound

Product 1

HCID 21105740HCID 21105740, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]-3-nitrobenzoic acid (0.200 g), 5% palladium on carbon (0.200 g) and tetrahydrofuran (20 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-t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (0.120 g, yield 67%). Recrystallization from hexane-ethyl acetate gave yellow prism crystals. melting point: 266–268° 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-939dafa60465483092215065774a2f35
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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