Ammonium formate → 2-Amino-1-(3-methoxyphenyl)ethanol

HRID 1673089Notes

Reaction equation

HRID 1673089 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]([OH:18])[CH2:14][N+:15]([O-])=O)[CH:10]=[CH:11][CH:12]=1>O1CCCC1.CO.[C].[Pd]>[NH2:15][CH2:14][CH:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[CH:8]=1)[OH:18]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 15528422HCID 15528422, compound

Product 1

HCID 5866792-Amino-1-(3-methoxyphenyl)ethanolYield 72.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium-carbon (10%, 0.64 g) and ammonium formate (4.8 g) were added to a mixed solution of the compound of Example B142 (3.0 g, 15 mmol) in tetrahydrofuran (43 ml) and methanol (43 ml), and this mixture was stirred at room temperature for 18 hours. The catalyst was removed by filtration, the filtrate was diluted with ether, precipitates were removed by filtration, and the obtained filtrate was concentrated to give the title compound (1.82 g). This compound was used in the following reaction without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. additionthe filtrate was diluted with ether
  3. customprecipitates
  4. customwere removed by filtration
  5. concentrationthe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-f47ab0365486467cba976d98db59c8f0
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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