1-Fluoro-4-methoxy-5-methyl-2-nitrobenzene → 2-Fluoro-5-methoxy-4-methylaniline

HRID 2065731Notes

Reaction equation

HRID 2065731 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N+:11]([O-])=O.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH2:11]

Participants

5

Reactant 2

HCID 598501391-Fluoro-4-methoxy-5-methyl-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 593777852-Fluoro-5-methoxy-4-methylanilineYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Fluoro-4-methoxy-5-methyl-2-nitro-benzene (1.18 g, 6.4 mmol) was dissolved in 40 ml of methanol at room temperature. 10% Palladium on Carbon (200 mg) was added and the mixture was stirred under a balloon of hydrogen overnight. The mixture was filtered through celite. The filtrate was concentrated in vacuo to give 2-fluoro-5-methoxy-4-methyl-phenylamine (990 mg, quantitative) as a solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-061e7ecb57e34f22841fa4c91f883731
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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