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

HRID 1384536Notes

Reaction equation

HRID 1384536 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. 1H NMR Spectrum: (DMSOd6) 1.94(s, 3H); 4.67(s, 2H); 6.22(d, 1H); 6.65(d, 1H); 8.68(s, 1H) MS-ESI: 142 []+

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-d5a43c6cd9d54abc8bf21bb8b102a382
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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