2-Morpholin-4-yl-5-nitrophenol → 5-Amino-2-morpholinophenol

HRID 929687Notes

Reaction equation

HRID 929687 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[OH:16])[CH2:3][CH2:2]1>[Pd].C(O)C.[H][H]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[C:8]([OH:16])[CH:9]=1

Participants

5

Reactant 1

HCID 230715652-Morpholin-4-yl-5-nitrophenol

Product 1

HCID 539059685-Amino-2-morpholinophenolYield 105%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

10% Palladium on carbon (10 mg, 0.892 mmol) was added to 2-morpholino-5-nitrophenol (prepared as described herein above; 200 mg, 0.892 mmol) in ethanol (20 mL), hydrogen gas was added (40 psi), and the reaction allowed to proceed for 12 h at room temperature. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture filtered through Celite®, and the solvent removed in vacuo. The residue was purified by flash column chromatography (2% CH3OH/CH2Cl2) to provide the title compound 5-amino-2-morpholinophenol (200 mg, 0.937 mmol, 105% yield) as a solid.

Workup

  1. additionwas added (40 psi)
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture filtered through Celite®
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-c08b78cf3cda4d8abdf7fbec3f3950df
Source dataset
uspto-grants-2016_03
Patent number
US09296703B2

Reaction notes

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