3-Fluoro-4-nitroanisole → 2-Fluoro-4-methoxyaniline

HRID 1608919Notes

Reaction equation

HRID 1608919 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-])=O>[Pt]=O.C(O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10]

Participants

4

Reactant 1

HCID 5656543-Fluoro-4-nitroanisole

Product 1

HCID 37563832-Fluoro-4-methoxyanilineYield 93.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 11.4 grams (0.067 mole) of 2-fluoro-4-methoxynitrobenzene and 0.4 gram of platinum oxide catalyst in 100 mL of ethanol was placed in a hydrogenation bottle and hydrogenated at 50 psi using a Parr hydrogenator. The completion of the hydrogenation required about two hours. After this time the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure, yielding 8.8 grams of 2-fluoro-4-methoxyaniline. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customabout two hours
  2. filtrationAfter this time the reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f31fdc76d419407982678fe57403f485
Source dataset
uspto-grants-1995_03
Patent number
US05399543

Reaction notes

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