HCID 22934560, compound → HCID 22934557, compound

HRID 1354460Notes

Reaction equation

HRID 1354460 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=2)=[N:12][N:11]=1)([O-])=O>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=2)=[N:12][N:11]=1

Participants

4

Reactant 1

HCID 22934560HCID 22934560, compound

Product 1

HCID 22934557HCID 22934557, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-[5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl]benzoate (2.00 g), 5%.palladium on carbon (0.4 g) and tetrahydrofuran (50 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 (hexane:ethyl acetate=9:1, volume ratio) to give ethyl 4-[5-(2-aminophenyl)-1,3,4-oxadiazol-2-yl]benzoate (0.23 g, yield 62%). Recrystallization from hexane-ethyl acetate gave pale-yellow prism crystals. melting point: 174–175° C.

Workup

  1. filtrationPalladium on carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1, volume ratio)

Sources & evidence

ORD record
ord-769d7198c9d04333a4b3aacfc6cf04b5
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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