Water → 4-Fluoro-2-methoxyaniline

HRID 1282081Notes

Reaction equation

HRID 1282081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.O.NN.O.CCCCCC>C(O)C.[Ni].C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 24654Hydrazine hydrate (1:1)HCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 135322284-Fluoro-2-methoxyanilineYield 89.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-2-methoxynitrobenzene (4.2 g) in ethanol (50 ml) was added Raney-nickel (0.4 g) at room temperature. To this solution was added dropwise hydrazine monohydrate (6 ml) under ice-cooling. This reaction mixture was stirred at room temperature for 1 hr and passed through Celite. The solvent was evaporated to give an oil. The oil was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated to give a brown oil. The oil was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=1:1) to give the title compound (3.1 g) as a brown oil.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. customto give an oil
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customto give a brown oil

Sources & evidence

ORD record
ord-812dc03785894dd09b0fb574f66cbf7c
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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