5-Methoxy-3-(4-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one → 3-(4-Aminophenyl)-5-methoxy-1,3,4-oxadiazol-2(3H)-one

HRID 840726Notes

Reaction equation

HRID 840726 reaction equation
[CH3:1][O:2][C:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:4]=1.[H][H]>[Pd].CO>[CH3:1][O:2][C:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[N:4]=1

Participants

5

Reactant 2

HCID 102361585-Methoxy-3-(4-nitrophenyl)-1,3,4-oxadiazol-2(3H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 99207173-(4-Aminophenyl)-5-methoxy-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture consisting of 1.4 g of 5-methoxy-3-(4-nitrophenyl)-3H-(1,3,4)oxadiazol-2-one, 0.5 g of Pd/C and 20ml of methanol was hydrogenated under atmospheric pressure at room temperature until the calculated amount of hydrogen had been taken up. The catalyst was then filtered off, and the solution was concentrated in vacuo. The remaining semisolid residue was stirred with isopropanol and filtered off with suction.

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe solution was concentrated in vacuo
  3. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-c9fe2b85bfef4974a91af7e163da366c
Source dataset
uspto-grants-2002_04
Patent number
US06369088B2

Reaction notes

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