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

HRID 973936Notes

Reaction equation

HRID 973936 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 ar 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-9558d2c21b4c431aac7b8e1a0b9d3b34
Source dataset
uspto-grants-1991_11
Patent number
US05066653

Reaction notes

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