2,4-Dichloro-5-fluoro-3-methoxynitrobenzene → 2,4-Dichloro-5-fluoro-3-methoxyaniline

HRID 47902Notes

Reaction equation

HRID 47902 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[C:5]([F:11])=[CH:4][C:3]=1[N+:12]([O-])=O.[H][H]>CO.[Pd]>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[C:5]([F:11])=[CH:4][C:3]=1[NH2:12]

Participants

5

Reactant 2

HCID 234317792,4-Dichloro-5-fluoro-3-methoxynitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 234317892,4-Dichloro-5-fluoro-3-methoxyanilineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

72.0 g of 2,4-dichloro-5-fluoro-3-methoxynitrobenzene (0.30 mol) and 2.65 g of Pd/C in 500 ml of methanol were hydrogenated under 3 Mpa (hydrogen pressure) at 60° C. for 3 hours. The reactant was cooled to room temperature. The catalyst was filtered out, and the solvent was evaporated to give 58.5 g of 2,4-dichloro-5-fluoro-3-methoxyaniline (0.279 mol) in 92.9% yield.

Workup

  1. filtrationThe catalyst was filtered out
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-626062908a0840f4a6078593e9cd23c7
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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