2-Fluoro-4-(methoxymethoxy)-1-nitrobenzene → 2-Fluoro-4-(methoxymethoxy)aniline

HRID 1967550Notes

Reaction equation

HRID 1967550 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-])=O.[H][H]>[C].[Pd].C(O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[NH2:12]

Participants

5

Reactant 2

HCID 199324002-Fluoro-4-(methoxymethoxy)-1-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 653652452-Fluoro-4-(methoxymethoxy)anilineYield 73.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% Palladium-carbon (390 mg) as a catalyst was added to an ethanol (100 mL) solution of 2-fluoro-4-(methoxymethoxy)-1-nitrobenzene (3.86 g), and stirred overnight in a hydrogen atmosphere at room temperature. The catalyst was removed through filtration, the solvent was evaporated off under reduced pressure, and the resulting residue was purified through silica gel column chromatography (methanol/chloroform=from 0% to 20%, gradient) to give the entitled compound (2.40 g, 73%) as a brown oily substance.

Workup

  1. customThe catalyst was removed through filtration
  2. customthe solvent was evaporated off under reduced pressure
  3. customthe resulting residue was purified through silica gel column chromatography (methanol/chloroform=from 0% to 20%, gradient)

Sources & evidence

ORD record
ord-fd2e952d47e043c28f0253db39672f97
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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