Ethanol → 4-(Oxazol-4-yl)aniline

HRID 1070830Notes

Reaction equation

HRID 1070830 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][O:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)C.[H][H]>[C].[Pd].O1CCCC1>[O:13]1[CH:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[N:11]=[CH:12]1

Participants

6

Reactant 3

HCID 702EthanolHCID 145677974-(4-Nitrophenyl)oxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 223978534-(Oxazol-4-yl)aniline

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5% Palladium-carbon powder was added to a suspension of 4-(4-nitrophenyl)-1,3-oxazole in mixture of ethanol and tetrahydrofuran, and the reaction mixture was stirred under 1 atm of hydrogen at ambient temperature for 12 hours. The reaction mixture was filtered through Celite, and the resulting filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography, to obtain [4-(1,3-oxazol-4-yl)phenyl]amine (pale yellow solid). Electron Impact-MS (M)+:160.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95af47684b0e4769aaa2c925c5fec751
Source dataset
uspto-grants-2005_06
Patent number
US06903125B2

Reaction notes

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