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

HRID 1971475Notes

Reaction equation

HRID 1971475 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>CO.[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-methoxyanilineYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-fluoro-1-methoxy-2-nitro-benzene (85 g, 0.50 mol) in methanol (300 mL) containing palladium on carbon (10%, 8 g) was stirred for 15 hours under an atmosphere of hydrogen. The catalyst was filtered and the filtrate was evaporated to dryness to give the crude product (61.5 g, 0.436 mol, 87%), which was used directly in the next step.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6071b6f20cd84cc79c07d00ddeb26057
Source dataset
uspto-grants-2013_04
Patent number
US08431605B2

Reaction notes

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