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

HRID 2223459Notes

Reaction equation

HRID 2223459 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-e9b7950541c3491ab4ad99f40b44d97b
Source dataset
uspto-grants-2008_05
Patent number
US07375204B2

Reaction notes

Loading…