Acetic Acid → [3-(3,5-Dimethyl-4-isoxazolyl)-4-(methyloxy)phenyl]amine

HRID 1042975Notes

Reaction equation

HRID 1042975 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=2[O:16][CH3:17])=[C:5]([CH3:18])[O:4][N:3]=1.CC(O)=O>C(O)C.[Pd]>[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][C:8]=2[O:16][CH3:17])[NH2:13])=[C:5]([CH3:18])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 574655703,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole

Product 1

HCID 57465571[3-(3,5-Dimethyl-4-isoxazolyl)-4-(methyloxy)phenyl]amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3,5-dimethyl-4-[2-(methoxy)-5-nitrophenyl]isoxazole (for a preparation see intermediate 3, 1.7 g, 6.85 mmol, 1 eq.) in ethanol (170 ml), was added Pd/C (10% on carbon, 85 mg) and the reaction was stirred under hydrogen for 4 h. AcOH (1.7 ml) was added and the reaction was hydrogenated for 20 h. After filtration, the solvent was evaporated in vacuo. The crude compound was dissolved into DCM and washed with saturated aqueous Sodium hydrogen carbonate, dried over Na2SO4, filtered and evaporated. The title compound was obtained as a red oil (1.38 g, 88%). GC/MS m/z: 218.

Workup

  1. waitthe reaction was hydrogenated for 20 h
  2. filtrationAfter filtration
  3. customthe solvent was evaporated in vacuo
  4. dissolutionThe crude compound was dissolved into DCM
  5. washwashed with saturated aqueous Sodium hydrogen carbonate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-238f16b1c8054d3b9fdea269baeb7259
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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