Sodium Hydroxide → 5-Amino-4-fluoro-2-methylphenol
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
Product 1
Reagents, catalysts & solvents 3
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
- temperaturewas heated
- temperatureat reflux for 4 hours
- temperatureto cool
- extractionextracted with ethyl acetate (100 ml)
- extractionThe ethyl acetate extract
- dry with materialwas dried (MgSO4)
- customthe solvent removed by evaporation
Sources & evidence
- ORD record
- ord-994883380a214f47b45d3a084572d5ee
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087602B2
Reaction notes
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