[3-(4-Nitro-phenyl)-isoxazol-5-YL]-methanol → [3-(4-Aminophenyl)-1,2-oxazol-5-yl]methanol

HRID 72321Notes

Reaction equation

HRID 72321 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([CH2:15][OH:16])[O:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:14]=[C:13]([CH2:15][OH:16])[O:12][N:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 12007730[3-(4-Nitro-phenyl)-isoxazol-5-YL]-methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 55255855[3-(4-Aminophenyl)-1,2-oxazol-5-yl]methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[3-(4-nitro-phenyl)-isoxazol-5-yl]-methanol (300 mg, 1.58 mmol) was placed in a 250-ml Parr reactor flask, to which were added 50 ml of ethanol and 10 wt % Pd/C. The mixture was reacted under 40 psi of hydrogen in the Parr reactor for about 1 hour. The completion of the reaction was confirmed by TLC, and then a filtrate by means of a celite placed was distilled under reduced pressure to obtain a yellow solid compound. This was recrystallized from ethyl acetate/hexane (1:2) to obtain [3-(4-amino-phenyl)-isoxazol-5-yl]-methanol in a yellow solid state.

Workup

  1. distillationa filtrate by means of a celite placed was distilled under reduced pressure
  2. customto obtain a yellow solid compound
  3. customThis was recrystallized from ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-62d5eabe989e409aa27cca3bcf5cfc4a
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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