2-Fluoro-1,3-dimethyl-5-nitrobenzene → 4-Fluoro-3,5-dimethylaniline

HRID 2255005Notes

Reaction equation

HRID 2255005 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[C:6]([CH3:9])[C:7]=1[F:8].[H][H]>CO.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:9])[C:7]=1[F:8])[NH2:10]

Participants

5

Reactant 2

HCID 113672322-Fluoro-1,3-dimethyl-5-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 191033484-Fluoro-3,5-dimethylanilineYield 99.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 3 liters of methanol was dissolved 15 g of this 3,5-dimethyl-4-fluoro-1-nitrobenzene, and the resulting solution was treated with nitrogen to replace the air, after which 10 g of palladium carbon was added and catalytic reduction with hydrogen gas was carried out. After completion of the reaction, the insoluble materials were filtered off and the filtrate was concentrated to obtain 12.3 g of 3,5-dimethyl-4-fluoroaniline.

Workup

  1. additionthe resulting solution was treated with nitrogen
  2. customAfter completion of the reaction
  3. filtrationthe insoluble materials were filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-76836148507243d98949c062c5329b09
Source dataset
uspto-grants-1993_08
Patent number
US05238818

Reaction notes

Loading…