1-Fluoro-2-methoxy-4-nitrobenzene → 4-Fluoro-3-methoxyaniline

HRID 442264Notes

Reaction equation

HRID 442264 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12].[H][H]>[Pd].O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 144519681-Fluoro-2-methoxy-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 27745334-Fluoro-3-methoxyaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 10 grams of 2-fluoro-5-nitroanisole and 100 ml. of dioxane is reduced catalytically under 40 p.s.i. of hydrogen and 1.0 gram of 5% Pd/C. After the uptake of hydrogen ceases, the catalyst is filtered, and the filtrate is concentrated in vacuo to yield 4-fluoro-3-methoxyaniline.

Workup

  1. filtrationAfter the uptake of hydrogen ceases, the catalyst is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-9ac8f6ce11bc48d6b36b1c2544316579
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

Loading…