Tetrahydrofuran → HCID 22934534, compound

HRID 1354474Notes

Reaction equation

HRID 1354474 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=3[N+:23]([O-])=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.O1CCCC1>[Pd].C(OCC)(=O)C>[NH2:23][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:13]=1[C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:12]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 22934569HCID 22934569, compound

Product 1

HCID 22934534HCID 22934534, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3-nitrobenzoate (0.700 g), 5% palladium on carbon (0.700 g), tetrahydrofuran (15 ml) and ethyl acetate (30 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=3:1, volume ratio) to give methyl 3-amino-4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]benzoate (0.50 g, yield 79%). Recrystallization from hexane-ethyl acetate gave colorless prism crystals. melting point: 227–228° 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=3:1, volume ratio)

Sources & evidence

ORD record
ord-cd7dbbcc65674e52b543f700ec257240
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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