1-(2-Fluoro-5-nitrophenyl)ethan-1-one → 1-(5-Amino-2-fluorophenyl)ethanone

HRID 2307428Notes

Reaction equation

HRID 2307428 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]>C(O)C.[Pt]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:11](=[O:13])[CH3:12])[CH:4]=1

Participants

4

Reactant 1

HCID 27810671-(2-Fluoro-5-nitrophenyl)ethan-1-one

Product 1

HCID 27811251-(5-Amino-2-fluorophenyl)ethanoneYield 58.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(2-fluoro-5-nitro-phenyl)ethanone (7.3 g) and 5% Pt(S)/C (730 mg) in ethanol (50 mL) was hydrogenated at 50 psi for 20 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash chromatography (33% ethyl acetate in hexane) to give the title compound as a solid (3.56 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel flash chromatography (33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-182da13eea294ed5b46a82d275e03cbf
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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