2-(4-Nitrophenyl)oxazole → 4-(1,3-Oxazol-2-yl)aniline

HRID 450063Notes

Reaction equation

HRID 450063 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[O:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 109762762-(4-Nitrophenyl)oxazole

Product 1

HCID 123717394-(1,3-Oxazol-2-yl)anilineYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(4-nitro-phenyl)-oxazole (400 mg, 2.1 mmol) in methanol (10 ml) was hydrogenated over 10% Pd/C at 30 psi until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to give a residue which was purified by column chromatography using ethyl acetate/pet ether (3:7) to yield 4-oxazol-2-yl-phenylamine (300 mg, 89%).

Workup

  1. filtrationThe reaction mixture was then filtered over celite and
  2. concentrationconcentrated
  3. customto give a residue which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a98a99afd6534c989164d7913d7a956d
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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