4-(2,5-Difluoro-4-nitrophenyl)morpholine → 2,5-Difluoro-4-(morpholin-4-yl)aniline

HRID 2089893Notes

Reaction equation

HRID 2089893 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CCO.[Pd]>[F:11][C:5]1[CH:4]=[C:3]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:2]([F:1])=[CH:7][C:6]=1[NH2:8]

Participants

4

Reactant 1

HCID 580722644-(2,5-Difluoro-4-nitrophenyl)morpholine

Product 1

HCID 580723362,5-Difluoro-4-(morpholin-4-yl)anilineYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(2,5-difluoro-4-nitrophenyl)morpholine (11 g, 44 mmol) and 10% Pd—C (50% wet, 1.1 g) in EtOH (150 mL) was hydrogenated for 5 h at room temperature. The reaction mixture was filtered by celite, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from iPr2O/AcOEt to give the title compound (8.6 g, 91% yield) as a pale red powder: 1H NMR (300 MHz, DMSO-d6): δ ppm 2.66-2.95 (4H, m), 3.56-3.83 (4H, m), 5.00 (2H, s), 6.55 (1H, dd, J=13.8, 8.5 Hz), 6.77 (1H, dd, J=12.8, 8.3 Hz). LC-MS (ESI) m/z 215 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered by celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from iPr2O/AcOEt

Sources & evidence

ORD record
ord-b539417b6b3849b5b581a08151581fb3
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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