Ethyl 4-nitro-3-phenyl-1,2-oxazole-5-carboxylate → HCID 13494471, compound

HRID 1693550Notes

Reaction equation

HRID 1693550 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[N+:17]([O-])=O)=[O:5])[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:7]=1[NH2:17])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 13487955Ethyl 4-nitro-3-phenyl-1,2-oxazole-5-carboxylate

Product 1

HCID 13494471HCID 13494471, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-nitro-3-phenyl-isoxazole-5-carboxylic acid ethyl ester (62.3 mg, 0.238 mmol) in EtOH (2.0 mL) is added Raney Ni and the mixture is stirred under hydrogen (balloon) for overnight. The reaction mixture is then filtered through celite and evaporated in vacuo to provide crude 4-amino-3-phenyl-isoxazole-5-carboxylic acid ethyl ester (53.3 mg, 97% yield); HPLC-MS calculated for C12H12N2O3 (M+H+) 233.1. Found: 233.1.

Workup

  1. filtrationThe reaction mixture is then filtered through celite
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-ccb07bb6fad84d53832811f03e4babaf
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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