2-Chloro-4-fluoro-5-nitrotoluene → 4-Chloro-2-fluoro-5-methylaniline

HRID 231407

Reaction equation

HRID 231407 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[CH3:12].[H][H]>C(O)(=O)C.[Pt]>[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([NH2:9])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 101039792-Chloro-4-fluoro-5-nitrotolueneHCID 178418361HCID 178418361, compound

Product 1

HCID 141574954-Chloro-2-fluoro-5-methylaniline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-chloro-4-fluoro-5-nitrotoluene (30.0 g, 0.158 mole) in glacial acetic acid (150 ml) was added to a 250 ml Parr bottle which contained platinum IV oxide (0.4 g). The Parr bottle was placed on a Parr hydrogenation apparatus and charged with hydrogen. The reaction mixture was allowed to shake until hydrogen absorption ceased. The catalyst was removed by vacuum filtration. The filtrate containing 4-chloro-2-fluoro-5-methylaniline was used in the following step. This reaction was repeated several times.

Workup

  1. customto shake until hydrogen absorption
  2. customThe catalyst was removed by vacuum filtration
  3. additionThe filtrate containing 4-chloro-2-fluoro-5-methylaniline

Sources & evidence

ORD record
ord-9b0c3425db194681af283128da57f87f
Source dataset
uspto-grants-1989_07
Patent number
US04846875

Linked notes

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