5-(3-Nitrophenyl)oxazole → 3-(1,3-Oxazol-5-yl)aniline

HRID 2409916Notes

Reaction equation

HRID 2409916 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:14][CH:13]=[N:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[O:14]1[C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[NH2:1])=[CH:11][N:12]=[CH:13]1

Participants

4

Reactant 1

HCID 27370675-(3-Nitrophenyl)oxazole

Product 1

HCID 27392893-(1,3-Oxazol-5-yl)anilineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (0.60 gm, 0.56 mmol) was added to a solution of 5-(3-Nitrophenyl)oxazole (5.80 gm, 30.50 mmol) in MeOH (122 mL). A H2 atmosphere was then introduced via balloon. After 24 h the reaction mixture was filtered through Celite. The catalyst was rinsed with MeOH and the filtrate was concentrated to give the product 3-(oxazol-5-yl)aniline (4.82 gm, 30.10 mmol, 99% yield) as a white solid. Anal. Calcd. for C9H6N2O3 m/z 160.1, found: 161.1 (M+H)+. Crude product was used without purification.

Workup

  1. additionA H2 atmosphere was then introduced via balloon
  2. filtrationAfter 24 h the reaction mixture was filtered through Celite
  3. washThe catalyst was rinsed with MeOH
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d3a6bb00c2f54760b16b57aea0aaf322
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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