Ammonium formate → 3-Fluoro-4-morpholinoaniline

HRID 245306Notes

Reaction equation

HRID 245306 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[NH2:14]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 29054894-(2-Fluoro-4-nitrophenyl)morpholine

Product 1

HCID 14853303-Fluoro-4-morpholinoanilineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd—C 4.0 g was added to 3-fluoro-4-morpholinyl nitrobenzene (40 g, 177 mmol), ammonium formate (50 g, 793 mmol) in 200 mL of ethyl acetate and stirred at 45˜50° C. for 8 h until the completion of the reaction. The mixture was then filtrated and separated by water. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 33 g of solid in 95% yield.

Workup

  1. filtrationThe mixture was then filtrated
  2. customseparated by water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1c93aff449f8492a9eec693a741f577d
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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