4-(2-Methoxy-4-nitrophenyl)morpholine → 3-Methoxy-4-(morpholin-4-yl)aniline

HRID 495465Notes

Reaction equation

HRID 495465 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 219364654-(2-Methoxy-4-nitrophenyl)morpholine

Product 1

HCID 219364683-Methoxy-4-(morpholin-4-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-(2-methoxy-4-nitro-phenyl)-morpholine (Step A, 1.0 g, 4.2 mmol) in EtOH (25 mL) at 20° C. was added Pd/C (100 mg). The flask was capped with a rubber septum and H2 pressure applied through a balloon/needle. The reaction was stirred at 20° C. for 12 h, filtered through sand/Celite® and concentrated. Purification by chromatography of the crude mixture (97:3 CH2Cl2:MeOH) afforded 3-methoxy-4-morpholin-4-yl-phenylamine as a purple solid.

Workup

  1. customThe flask was capped with a rubber septum and H2 pressure
  2. filtrationfiltered through sand/Celite®
  3. concentrationconcentrated
  4. customPurification by chromatography of the crude mixture (97:3 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-f9491ab84cdb4d779c69f2eaf66fc9d5
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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