5-(4-Nitrophenyl)-1,3,4-oxadiazol-2-ol → 5-(4-aminophenyl)-1,3,4-oxadiazol-2-ol

HRID 1164810Notes

Reaction equation

HRID 1164810 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[NH:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][C:13](=[O:15])[NH:12][N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 127772585-(4-Nitrophenyl)-1,3,4-oxadiazol-2-ol

Product 1

HCID 2796305-(4-aminophenyl)-1,3,4-oxadiazol-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(4-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one, (0.65 g) in ethanol (100 ml) was hydrogenated at 276 kPa (40 p.s.i.) in the presence of palladium on carbon at room temperature for one hour. The reaction mixture was filtered, the filtrate was evaporated to dryness and the resultant yellow solid was recrystallised from ethanol to afford (5-(4-aminophenyl)-1,3,4-oxadiazol-2(3H)-one, 0.46 g, m.p. 172°-173° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customthe resultant yellow solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-b9cddf5a035b4b37b04221531e0c16c0
Source dataset
uspto-grants-1990_03
Patent number
US04906628

Reaction notes

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