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

HRID 2388106Notes

Reaction equation

HRID 2388106 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-a742075482d54aba8861ee5869992073
Source dataset
uspto-grants-2012_09
Patent number
US08269011B2

Reaction notes

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