2-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole → 4-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline

HRID 2374149Notes

Reaction equation

HRID 2374149 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[N:5][N:6]=1>CO.[Pd]>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[N:5][N:6]=1

Participants

4

Reactant 1

HCID 5404162-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole

Product 1

HCID 195422444-(5-Methyl-1,3,4-oxadiazol-2-yl)anilineYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-5-(4-nitro-phenyl)-[1,3,4]oxadiazole (0.930 g, 4.54 mmol) was dissolved in MeOH. To this was added 10% palladium on carbon (0.06 g) and the mixture shaken under hydrogen pressure (35 psi, Parr apparatus) until the reaction was complete (LCMS monitored). The solids were filtered off and rinsed with MeOH. The filtrate was concentrated to give the title compound (0.76 g). MS (ESI+) for m/z 176 (M+H)+.

Workup

  1. filtrationThe solids were filtered off
  2. washrinsed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-156ecb1421ed4942b5a7c4f8641c5de6
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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