Sodium Hydroxide → 5-Amino-4-fluoro-2-methylphenol

HRID 1057336Notes

Reaction equation

HRID 1057336 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([OH:11])=[C:4]([CH3:12])[CH:3]=1.[OH-].[Na+]>O.[Fe].S([O-])([O-])(=O)=O.[Fe+2]>[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([OH:11])=[CH:6][C:7]=1[NH2:8]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 108210594-Fluoro-2-methyl-5-nitrophenol

Product 1

HCID 101540985-Amino-4-fluoro-2-methylphenolYield 47%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 24393Ferrous SulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-fluoro-2-methyl-5-nitrophenol (2.1 g, 13 mmol), iron powder (1 g, 18 mmol) and iron(II)sulphate (1.5 g, 10 mmol) in water (40 ml) was heated at reflux for 4 hours. The reaction mixture was allowed to cool, neutralised with 2M aqueous sodium hydroxide solution and extracted with ethyl acetate (100 ml). The ethyl acetate extract was dried (MgSO4) and the solvent removed by evaporation to give 2-fluoro-5-hydroxy-4-methylaniline (0.8 g, 47%) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate (100 ml)
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried (MgSO4)
  7. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-2f53e854dce341318f0b497cb051a837
Source dataset
uspto-grants-2003_02
Patent number
US06514971B1

Reaction notes

Loading…