2-Fluoro-4-nitroanisole → 3-Fluoro-4-methoxyaniline

HRID 1723360Notes

Reaction equation

HRID 1723360 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([F:12])[CH:5]=1)([O-])=O>O1CCOCC1.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([F:12])[CH:5]=1

Participants

4

Reactant 1

HCID 2231042-Fluoro-4-nitroanisole

Product 1

HCID 5811103-Fluoro-4-methoxyanilineYield 104.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

[I] 2 g of 5% palladium carbon was added to a solution prepared by dissolving 10 g of 4-nitro-2-fluoroanisol in 150 ml of 1,4-dioxane, and the mixture was subjected to catalytic reduction under a hydrogen gas pressure of 4 kg/cm2 at room temperature for 30 minutes. After the completion of the reaction, palladium carbon was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 8.6 g of 4-amino-2-fluoroanisol.

Workup

  1. customprepared
  2. customat room temperature
  3. customfor 30 minutes
  4. customwas removed by filtration
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8af217f0d90949e69f000f982e634be7
Source dataset
uspto-grants-1989_08
Patent number
US04861799

Reaction notes

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