Hydrochloric Acid → 2-Amino-4'-methoxyacetophenone

HRID 2367364Notes

Reaction equation

HRID 2367364 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6])=[N+]=[N-].[ClH:15]>[Pd].CO>[ClH:15].[NH2:1][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 109978352-Azido-1-[4-(methyloxy)phenyl]ethanone

Product 2

HCID 313Hydrochloric AcidHCID 4128892-Amino-4'-methoxyacetophenoneYield 115.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Palladium on carbon (10 wt %, 1.67 g, 1.57 mmol) was added to a solution of 2-azido-1-[4-(methyloxy)phenyl]ethanone (3.0 g, 15.69 mmol) and hydrochloric acid (6.62 mL, 78 mmol) in CH3OH (90 mL) under nitrogen, and the reaction mixture was stirred under hydrogen overnight at 25° C. The mixture was filtered, washed by EtOAc (150 mL), and concentrated to afford an HCl salt of the title compound (3.0 g) as a yellow solid. LC-MS (ES) m/z=166 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed by EtOAc (150 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-802e1c3052a143bb97e2001e58e30178
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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