5-(4-nitrophenyl)-3H-1,3-oxazol-2-one → 5-(4-Aminophenyl)-1,3-oxazol-2(3H)-one

HRID 56615Notes

Reaction equation

HRID 56615 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[NH:12][CH: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][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 8221335-(4-nitrophenyl)-3H-1,3-oxazol-2-one

Product 1

HCID 1176227935-(4-Aminophenyl)-1,3-oxazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.1 g (5.4 mmol) of 5-(4-nitrophenyl)-1,3-oxazol-2(3H)-one in 40 ml of ethanol was hydrogenated in the presence of 111 mg of palladium (10% on activated carbon) at RT and standard pressure for 5 d. The reaction mixture was then filtered through Celite and the residue was washed with ethanol. The combined filtrates were concentrated under reduced pressure. The residue was used for the next step without further purification. Yield: 626 mg (purity 88%, 58% of theory)

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washthe residue was washed with ethanol
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. customThe residue was used for the next step without further purification

Sources & evidence

ORD record
ord-30bea0a6042a4218bea4e67ef947e621
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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