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

HRID 1985860Notes

Reaction equation

HRID 1985860 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 in ethanol is added concentrated HCl (aq) and 10% Pd/C (10 mol %). The mixture is stirred under hydrogen (H2) atmosphere at 45 psi for 1 hour. The mixture is filtered through celite and the celite cake is washed with copious amounts of methanol. The solvent is removed under reduce pressure and the resulting residue is triturated with diethyl ether, filtered and dried to give 2-amino-1-(4-fluoro-phenyl)-ethanone hydrochloride.

Workup

  1. filtrationThe mixture is filtered through celite
  2. washthe celite cake is washed with copious amounts of methanol
  3. customThe solvent is removed
  4. customthe resulting residue is triturated with diethyl ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-4b755aa187404d1b901285d9b14103ba
Source dataset
uspto-grants-2009_06
Patent number
US07547717B2

Reaction notes

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