2-Fluoro-n-(2-nitrophenyl)aniline → N1-(2-Fluorophenyl)benzene-1,2-diamine

HRID 1818770Notes

Reaction equation

HRID 1818770 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 2613812-Fluoro-n-(2-nitrophenyl)aniline

Product 1

HCID 19039441N1-(2-Fluorophenyl)benzene-1,2-diamineYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-fluoro-N-(2-nitrophenyl)aniline (1.4 g, 6.0 mmol) was dissolved in ethyl acetate (20 mL) and 10% palladium on activated carbon (150 mg) was added. The mixture was shaken under a hydrogen atmosphere (40 psi) for 2 hours. The mixture was filtered through a pad of Celite and concentrated to give N-(2-fluorophenyl)benzene-1,2-diamine (1.2 g) that was carried on directly to the next step.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8fa4c21c9b9a4c97acd2e6ca7c265470
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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