HCID 14834673, compound → 2,4,5-Trifluoro-3-methylaniline

HRID 2396940Notes

Reaction equation

HRID 2396940 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-])=O)=[C:4]([F:12])[C:3]=1[CH3:13]>[Pd].C(O)(=O)C>[F:12][C:4]1[C:3]([CH3:13])=[C:2]([F:1])[C:7]([F:8])=[CH:6][C:5]=1[NH2:9]

Participants

4

Reactant 1

HCID 14834673HCID 14834673, compound

Product 1

HCID 146512532,4,5-Trifluoro-3-methylanilineYield 77.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To acetic acid (350 ml) are added 5% Pd-C (3.5 g) and 2,3,6-trifluoro-5-nitrotoluene (35 g) and the mixture is subjected to catalytic reduction at room temperature under atomospheric pressure. 5% Pd-C is filtered off and the acetic acid is distilled off under reduced pressure. The residue is poured into ice-water, neutralized, extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the obtained residue is distilled under reduced pressure to give 2,4,5-trifluoro-3-methylaniline (22.86 g), as yellow crystals, b.p. 85° C./20 mmHg.

Workup

  1. customis subjected to catalytic reduction at room temperature under atomospheric pressure
  2. filtration5% Pd-C is filtered off
  3. distillationthe acetic acid is distilled off under reduced pressure
  4. additionThe residue is poured into ice-water
  5. extractionextracted with dichloromethane
  6. washthe extract is washed with water
  7. customdried
  8. distillationThe solvent is distilled off under reduced pressure
  9. distillationthe obtained residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-11cb1a3e7ff6427abd0f92bb86c2adb5
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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