HCID 15554721, compound → HCID 57897974, compound

HRID 1693545Notes

Reaction equation

HRID 1693545 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([N+:11]([O-])=O)=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:8][N:7]=1)=[O:5])[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([NH2:11])=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 15554721HCID 15554721, compound

Product 1

HCID 57897974HCID 57897974, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-nitro-5-phenyl-isoxazole-3-carboxylic acid ethyl ester (73.0 mg, 0.278 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-5-phenyl-isoxazole-3-carboxylic acid ethyl ester (61.7 mg, 95% 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-23b2320ddaaf44dbaccfd5cdcee5ce10
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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