2-Azido-1-(2-methoxyphenyl)ethanone → 2-Amino-1-(2-methoxyphenyl)ethanone

HRID 1616578Notes

Reaction equation

HRID 1616578 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:6])=[N+]=[N-]>CO.Cl.[Pd]>[NH2:1][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:6]

Participants

5

Reactant 1

HCID 252236542-Azido-1-(2-methoxyphenyl)ethanone

Product 1

HCID 198330252-Amino-1-(2-methoxyphenyl)ethanoneYield 122.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Dissolve 2-azido-1-(2-methoxy-phenyl)-ethanone (3.54 g, 18.5 mmol) in 1328 ml of MeOH and 9 ml of concentrated HCl. Add 943 mg of 10% Pd/C and expose the reaction mixture to 60 psi of H2 for 5 hours at ambient temperature. Filter the catalyst off through a pad of celite and concentrate the filtrate in vacuo to afford 3.74 g of crude 2-amino-1-(2-methoxyphenyl)-ethanone as the hydrochloride salt.

Workup

  1. customfor 5 hours
  2. customat ambient temperature
  3. filtrationFilter the catalyst off through a pad of celite
  4. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-299bcf5550164dee8c3b607e1bf77359
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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