3-Nitrophenylethyl alcohol → 2-(3-Aminophenyl)ethan-1-ol

HRID 2373631Notes

Reaction equation

HRID 2373631 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 1040583-Nitrophenylethyl alcoholHCID 2723923Ammonium formate

Product 1

HCID 149389872-(3-Aminophenyl)ethan-1-olYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(3-Nitrophenyl)ethanol (836 mg, 5.00 mmol) and Pd (10% on charcoal, 200 mg) were suspended in dry methanol (10 mL). After the addition of ammonium formate (1.450 g, 23 mmol) a slightly exothermic and effervescent reaction was observed. After stirring for 1 h at room temperature the mixture was filtered over celite. The filtrate was evaporated and the residue dissolved in ethyl acetate. After washing with saturated aqueous sodium hydrogencarboante solution, water and brine the organic layer was dried (magnesium sulfate) and the solvent removed under reduced pressure affording the title compound in 54% yield (373 mg) as a white solid.

Workup

  1. customeffervescent reaction
  2. filtrationwas filtered over celite
  3. customThe filtrate was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washAfter washing with saturated aqueous sodium hydrogencarboante solution, water and brine the organic layer
  6. dry with materialwas dried (magnesium sulfate)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3e18304114954352862fe066ab684ad7
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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