Morpholine, 4-(3-methoxy-4-nitrophenyl)- → 2-Methoxy-4-morpholinoaniline

HRID 1887689Notes

Reaction equation

HRID 1887689 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

3

Reactant 1

HCID 81388Morpholine, 4-(3-methoxy-4-nitrophenyl)-

Product 1

HCID 4149602-Methoxy-4-morpholinoanilineYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 L round bottom flask charged with 4-(3-methoxy-4-nitrophenyl)morpholine (15.7 g, 66 mmol) in 300 mL MeOH, was evacuated and then backfilled with argon. This sequence was repeated two additional times. The reaction vessel was kept under a stream of argon and Pd(C) (10%, 1.57 g) was added. After the addition of Pd (C) was complete the reaction vessel was evacuated and backfilled with hydrogen gas. This evacuation/backfill sequence was repeated twice. After 18 h the hydrogen gas was evacuated by introducing argon into the round bottom flask. The reaction mixture was filtered through a pad of Celite. The Celite was washed with 200 mL EtOAc. The volatiles were evaporated to yield 13.4 g of 2-methoxy-4-morpholinoaniline (64 mmol, 97%).

Workup

  1. customwas evacuated
  2. additionwas added
  3. additionAfter the addition of Pd (C)
  4. customwas evacuated
  5. customAfter 18 h the hydrogen gas was evacuated
  6. additionby introducing argon into the round bottom flask
  7. filtrationThe reaction mixture was filtered through a pad of Celite
  8. washThe Celite was washed with 200 mL EtOAc
  9. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-4b383b4618c44b1a9fd030c291f7142f
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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