4-Fluoro-2-nitroanisole → 5-Fluoro-2-methoxyaniline

HRID 1166239Notes

Reaction equation

HRID 1166239 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([NH2:10])[CH:3]=1

Participants

4

Reactant 1

HCID 5656564-Fluoro-2-nitroanisole

Product 1

HCID 2231055-Fluoro-2-methoxyaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-fluoro-2-nitroanisole (20.5 g, 120 mmol) in ethyl acetate (100 ml) was hydrogenated in a Parr shaker apparatus with 10% Pd on carbon (2 g) until a stable pressure reading was obtained. The reaction was filtered through Celite and concentrated under vacuum to an oil. The 4-fluoro-2-aminoanisole thus obtained (16.14 g, 96%) was used in the next step.

Workup

  1. customwas obtained
  2. filtrationThe reaction was filtered through Celite
  3. concentrationconcentrated under vacuum to an oil

Sources & evidence

ORD record
ord-a9cc32ebc3cf425aa2b6b315e3103a96
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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