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

HRID 68467

Reaction equation

HRID 68467 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-oneYield 37.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In an autoclave, 63 g (0.275 mol) of 4-(4-morpholin-3-onyl)nitrobenzene are dissolved in 200 ml of tetrahydrofuran, admixed with 3.1 g of Pd/C (5% ig) and hydrogenated at 70° C. and a hydrogen pressure of 50 bar for 8 h. The catalyst is filtered off, the solvent is then distilled off under reduced pressure and the product is purified by crystallization from ethyl acetate. 20 g of product are obtained as a colourless to bluish solid, in a yield of 37.6% of theory.

Workup

  1. filtrationThe catalyst is filtered off
  2. distillationthe solvent is then distilled off under reduced pressure
  3. customthe product is purified by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-5424d5fc9d7d43dda5c78c8b21573aaf
Source dataset
uspto-grants-2014_09
Patent number
US08822458B2

Linked notes

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