4-Fluoro-2-nitro-1-propoxybenzene → 5-Fluoro-2-propoxyaniline

HRID 238318Notes

Reaction equation

HRID 238318 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH3:11])=[C:4]([N+:12]([O-])=O)[CH:3]=1>[C].[Pd].C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH3:11])=[C:4]([CH:3]=1)[NH2:12]

Participants

4

Reactant 1

HCID 669171744-Fluoro-2-nitro-1-propoxybenzene

Product 1

HCID 261896335-Fluoro-2-propoxyanilineYield 86%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

4-Fluoro-2-nitro-1-propoxybenzene (2.0 g, 10.0 mmol) and 5% palladium carbon (750 mg) were added to ethanol (30 ml). Catalytic reduction was conducted at room temperature and atmospheric pressure (normal pressure). The catalyst was removed by celite filtration, and the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane, and dried over anhydrous magnesium sulfate. The resulting dry product was concentrated under reduced pressure to thereby obtain 1.45 g of oily red orange 5-fluoro-2-propoxyaniline (yield: 86%).

Workup

  1. customwas conducted at room temperature
  2. customThe catalyst was removed by celite filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe resulting dry product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2bca2d29664e45108427f2b2d3dd0d37
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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