4-(4-Nitrophenyl)-morpholin-3-ON → 4-(4-Aminophenyl)morpholin-3-one

HRID 1796941Notes

Reaction equation

HRID 1796941 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].[H][H]>O1CCCC1.[Pd]>[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7]

Participants

5

Reactant 2

HCID 114473754-(4-Nitrophenyl)-morpholin-3-ONHCID 178418361HCID 178418361, compound

Product 1

HCID 111948544-(4-Aminophenyl)morpholin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In an autoclave, 4-(4-morpholin-3-onyl)nitrobenzene (63 g, 0.275 mol) is dissolved in tetrahydrofuran (200 ml), Pd/C (3.1 g, 5%) is added and the mixture is hydrogenated at 70° C. and a hydrogen pressure of 50 bar for 8 hours. The catalyst is filtered off and the solvent is then distilled off under reduced pressure and the product is purified by crystallization from ethyl acetate. Yield: 20 g (colorless to bluish solid), 37.6% of theory. Alternatively, purification can also be carried out by chromatography (on silica gel, hexane/ethyl acetate mixture).

Workup

  1. customis hydrogenated at 70° C.
  2. filtrationThe catalyst is filtered off
  3. distillationthe solvent is then distilled off under reduced pressure
  4. customthe product is purified by crystallization from ethyl acetate
  5. customAlternatively, purification

Sources & evidence

ORD record
ord-df3b03be66ad4e578fd203a890f32673
Source dataset
uspto-grants-2006_04
Patent number
US07034017B2

Reaction notes

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