Tetrahydrofuran → HCID 21105738, compound

HRID 1354467Notes

Reaction equation

HRID 1354467 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=3[N+:22]([O-])=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.O1CCCC1>[Pd].C(OCC)(=O)C>[NH2:22][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][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]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 21105746HCID 21105746, compound

Product 1

HCID 21105738HCID 21105738, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3-nitrobenzoic acid (0.600 g), 5% palladium on carbon (0.600 g), tetrahydrofuran (30 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=4:1, volume ratio) to give 3-amino-4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]benzoic acid (0.15 g, yield 28%). Recrystallization from hexane-tetrahydrofuran gave yellow prism crystals. melting point: 294–296° C. (decomposition).

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=4:1, volume ratio)

Sources & evidence

ORD record
ord-cdeea18755e54ce8aa12250df315ca99
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

Loading…