Benzene, 1-fluoro-2-methyl-4-nitro- → 4-Fluoro-m-toluidine

HRID 902227Notes

Reaction equation

HRID 902227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH3:11].[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 2

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 679814-Fluoro-m-toluidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 20 g (129 mmol) of 2-fluoro-5-nitrotoluene in 400 mL of ethanol was added 2 g of 10% Pd—C. The mixture was shaken under 45 P.S.I. H2 until hydrogen uptake ceased. The catalyst was filtered away and washed with ethanol, then the combined filtrate and washings were concentrated to 15.2 g (94%) of a colorless oil.

Workup

  1. filtrationThe catalyst was filtered away
  2. washwashed with ethanol
  3. concentrationthe combined filtrate and washings were concentrated to 15.2 g (94%) of a colorless oil

Sources & evidence

ORD record
ord-e53a1eec7c3a4dacb01e801cc596e1ab
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Reaction notes

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