5-Fluoro-2-nitrotoluene → 4-Fluoro-2-methylaniline

HRID 376445Notes

Reaction equation

HRID 376445 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH3:8])[CH:7]=1.[H][H]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5](=[CH:4][CH:3]=1)[NH2:9]

Participants

5

Reactant 2

HCID 949565-Fluoro-2-nitrotolueneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 679824-Fluoro-2-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Fluoro-2-nitrotoluene (0.5 mole) in ethyl acetate (600 ml.) is hydrogenated at 40 p.s.i. of hydrogen over Pd/C catalyst (1%, 2 teaspoons) at room temperature until the theoretical amount of hydrogen has been taken up. The catalyst is filtered off, and the solvent evaporated to give the crude oil of 4-fluoro-2-toluidine.

Workup

  1. customat room temperature
  2. filtrationThe catalyst is filtered off
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-b84ada5cdbe7464b8e6e1bc1bdc7d936
Source dataset
uspto-grants-2000_02
Patent number
US06020379

Reaction notes

Loading…