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

HRID 349699Notes

Reaction equation

HRID 349699 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CO.O1CCCC1.O>[N:1]1([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 12532734-(3-Nitrophenyl)morpholine

Product 1

HCID 8477683-(Morpholin-4-yl)anilineYield 85.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A 500 mL roundbottom flask equipped with stir bar and 3-way stopcock charged with MeOH/tetrahydrofuran/water (200 mL of 2:1:1) was purged thoroughly with nitrogen. To this was added 1.0 g of 10% Pd/C followed by addition of 10 g (48.0 mmol) of 3-morpholinyl nitrobenzene. The mixture then was stirred under a hydrogen atmosphere for 4 days (1 atm). The reaction was filtered over GF/F filter paper and the filtrate concentrated in vacuo to remove MeOH and THF. The resulting solid was recovered by filtration, washed with water, air dried, then dried in vacuo to give 7.3 g (83% yield) of the desired aniline as beige crystals.

Workup

  1. customA 500 mL roundbottom flask equipped
  2. customwas purged thoroughly with nitrogen
  3. additionTo this was added 1.0 g of 10% Pd/C
  4. stirringThe mixture then was stirred under a hydrogen atmosphere for 4 days (1 atm)
  5. filtrationThe reaction was filtered over GF/F
  6. filtrationfilter paper
  7. concentrationthe filtrate concentrated in vacuo
  8. customto remove MeOH and THF
  9. filtrationThe resulting solid was recovered by filtration
  10. washwashed with water, air
  11. customdried
  12. customdried in vacuo

Sources & evidence

ORD record
ord-538846cd2b8245489c44f2a9a5fb8c6d
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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