HCID 12371736, compound → 2-(1,3-Oxazol-2-yl)aniline

HRID 746153Notes

Reaction equation

HRID 746153 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:11][CH:12]=[CH:13][N:14]=1)([O-])=O.[H][H]>[Ni].C(O)C>[O:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 12371736HCID 12371736, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 123717402-(1,3-Oxazol-2-yl)anilineYield 108.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To 19.0 g of 2-(2-nitrophenyl)oxazole, (prepared by the procedure of W. E. Cass, J. Am. Chem. Soc., 64, 785 [1942]) 3.0 g of Raney-Nickel catalyst (purchased from Aldrich Chemical Company, Milwaukee, Wis. 53201) and 200 ml ethanol were combined and reduced at ambient temperature and at a H2 pressure of 5-50 psi on a Paar Hydrogenator until the hydrogen uptake ceased. The catalyst was filtered through celite under a blanket of nitrogen. The solvent was removed on a rotary evaporator. 17.4 g of crude product with m.p. 31°-32° was obtained and used in the next step.

Workup

  1. filtrationThe catalyst was filtered through celite under a blanket of nitrogen
  2. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-a077c7ed6e0849e8afc005f973f0471f
Source dataset
uspto-grants-1986_07
Patent number
US04602940

Reaction notes

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