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

HRID 614771Notes

Reaction equation

HRID 614771 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]>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

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

Product 1

HCID 679824-Fluoro-2-methylanilineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 125 g of 5-fluoro-2-nitrotoluene, 3.0 g of 5% palladium on carbon, and 200 ml of ethanol was reduced in a Parr hydrogenator under 46 p.s.i. hydrogen pressure. After hydrogen uptake had ceased, the catalyst was removed by filtration, and the ethanolic filtrate was evaporated under reduced pressure to give a colorless liquid. Purification by vacuum distillation yielded 85.7 g of 4-fluoro-2-methylaniline, b.p. 67°-71°/4.2 mm.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe ethanolic filtrate was evaporated under reduced pressure
  3. customto give a colorless liquid
  4. customPurification
  5. distillationby vacuum distillation

Sources & evidence

ORD record
ord-669f0296f11f4e02afb745b6ac090b74
Source dataset
uspto-grants-1979_03
Patent number
US04146625

Reaction notes

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