Ammonium formate → 2-Amino-1-[4-(methylthio)phenyl]ethanol

HRID 1908254Notes

Reaction equation

HRID 1908254 reaction equation
[N:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)[OH:6])=[N+]=[N-].C([O-])=O.[NH4+]>[Pd].CO>[NH2:1][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)[OH:6]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86635142HCID 86635142, compound

Product 1

HCID 167683402-Amino-1-[4-(methylthio)phenyl]ethanolYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
64 °C

Procedure

To a stirred rt suspension consisting of 2-azido-1-(4-methylsulfanyl-phenyl)-ethanol (104.6 mg, 0.50 mmol), 10% Pd/C (100 mg, 0.10 mmol) and MeOH (25 mL) was added ammonium formate (316 mg, 5.0 mmol) under a N2 atmosphere. The resulting mixture was heated at 64° C. for 2 h. After cooling to rt, the catalyst was removed by filtration through a pad of celite and the celite pad washed with MeOH. The filtrate was concentrated and purified (FCC) to yield the title compound (66 mg, 72%).

Workup

  1. customTo a stirred rt
  2. temperatureAfter cooling to rt
  3. customthe catalyst was removed by filtration through a pad of celite
  4. washthe celite pad washed with MeOH
  5. concentrationThe filtrate was concentrated
  6. custompurified (FCC)

Sources & evidence

ORD record
ord-163a3eecfe3a49e2af091b8bf9e71ece
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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