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

HRID 5805Notes

Reaction equation

HRID 5805 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-d3f1608a6b4f44cb9da8fc4248faeacd
Source dataset
uspto-grants-1993_09
Patent number
US05246928

Reaction notes

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