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

HRID 634661Notes

Reaction equation

HRID 634661 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 refluxed for 4 hours. The reaction mixture was allowed to cool, neutralised with 2M aqueous sodium hydroxide 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 refluxed for 4 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate (100 ml)
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (MgSO4)
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-ffc1d9800a944b9e88aaebe0a049648d
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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