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

HRID 7481

Reaction equation

HRID 7481 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-994883380a214f47b45d3a084572d5ee
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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