4-(2-Fluoro-4-nitrophenyl)morpholine → 3-Fluoro-4-morpholinoaniline

HRID 56089

Reaction equation

HRID 56089 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1COCC1.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[NH2:8]

Participants

4

Reactant 1

HCID 29054894-(2-Fluoro-4-nitrophenyl)morpholine

Product 1

HCID 14853303-Fluoro-4-morpholinoanilineYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenyl)morpholine (15.0 g, 66 mmol) in THF (100 mL) was added Pd/C (3.0 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give the title compound as a white solid (11.55 g, 89%).

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-51ae4d6c3bc14006be06859f8f9f4628
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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