Hydrochloric Acid → 2-Amino-1-(4-fluorophenyl)ethan-1-one hydrochloride

HRID 2221068Notes

Reaction equation

HRID 2221068 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6])=[N+]=[N-].[ClH:14]>C(O)C.[Pd]>[ClH:14].[NH2:1][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 139300882-Azido-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 132906662-Amino-1-(4-fluorophenyl)ethan-1-one hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-azido-1-(4-fluoro-phenyl)-ethanone (8.0 g, 44.7 mmol) in ethanol (125 mL) was added concentrated aqueous HCl (6 mL) and 10% Pd/C (10 mol %). The mixture was stirred under hydrogen (H2) atmosphere at 45 psi for 1 hour. The mixture was filtered through celite and the celite cake was washed with copious amounts of methanol. The solvent was under reduce pressure and the semisolid was triturated with diethyl ether, filtered and dried to give 2-amino-1-(4-fluoro-phenyl)-ethanone hydrochloride (5.0 g, 26.5 mmol) as a white crystalline solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe celite cake was washed with copious amounts of methanol
  3. customthe semisolid was triturated with diethyl ether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-07b6a0a4ccae4f1aa5721fde659604fc
Source dataset
uspto-grants-2008_05
Patent number
US07368467B2

Reaction notes

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