4-(3-Nitrophenyl)morpholine → 3-(Morpholin-4-yl)aniline

HRID 1356993Notes

Reaction equation

HRID 1356993 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>C(O)C.C(OCC)(=O)C.[Pd]>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[NH2:13])[CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 12532734-(3-Nitrophenyl)morpholine

Product 1

HCID 8477683-(Morpholin-4-yl)aniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Meta-morpholino nitrobenzene (2a) (2 g, 9.6 mmol) is hydrogenated in a mixture of ethanol and ethyl acetate (50 ml/10 ml), over 10% Pd on carbon (200 mg) for 1 hour. The catalyst is removed by filtration and the solvent removed by evaporation to yield a solid, which is dried under vacuum; ES+ (M+1) 179.35; mp 125.4-127.6° C.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent removed by evaporation
  3. customto yield a solid, which
  4. customis dried under vacuum

Sources & evidence

ORD record
ord-501f5331963946bba1585b2376d9a1e1
Source dataset
uspto-grants-2003_07
Patent number
US06589950B1

Reaction notes

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