Hydrochloric Acid → 2-Amino-1-(3-methoxyphenyl)ethanone

HRID 2367382Notes

Reaction equation

HRID 2367382 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[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][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=[O:6]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 187928632-Azido-1-(3-methoxyphenyl)ethanone

Product 2

HCID 313Hydrochloric AcidHCID 71760742-Amino-1-(3-methoxyphenyl)ethanoneYield 123.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Palladium on carbon (10 wt %, 10.41 g, 9.78 mmol) was added to a solution of 2-azido-1-[3-(methyloxy)phenyl]ethanone (1.87 g, 9.78 mmol) and hydrochloric acid (8.14 mL, 98 mmol) in CH3OH (50 mL) under nitrogen, and the reaction mixture was stirred under hydrogen overnight at 25° C. The mixture was filtered, washing with CH2Cl2 (50 mL) and CH3OH (100 mL), and then concentrated. Water (150 mL) was added, and the mixture was lyophilized to afford an HCl salt of the title compound (2.0 g) as a brown solid. LC-MS (ES) m/z=166 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with CH2Cl2 (50 mL) and CH3OH (100 mL)
  3. concentrationconcentrated
  4. additionWater (150 mL) was added

Sources & evidence

ORD record
ord-ab9fdc775cf34e7b93852829c5416a1a
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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