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

HRID 1460567Notes

Reaction equation

HRID 1460567 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.[C].[Pd]>[NH2:10][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

4

Reactant 1

HCID 5656564-Fluoro-2-nitroanisole

Product 1

HCID 2231055-Fluoro-2-methoxyanilineYield 100.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 20.5 g of 4-fluoro-2-nitroanisole in ethyl acetate was hydrogenated over 5% palladium carbon (2 g) at room temperature for 16 hours. The catalyst was removed by filtration and the filtrate evaporated to leave 17 g of the title compound as a brown oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e245d9a78ba942b289a188b1b19d29a9
Source dataset
uspto-grants-1991_12
Patent number
US05071863

Reaction notes

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