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

HRID 1487189Notes

Reaction equation

HRID 1487189 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>O1CCCC1.[Pd]>[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

4

Reactant 1

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

Product 1

HCID 4149602-Methoxy-4-morpholinoanilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(3-methoxy-4-nitrophenyl)morpholine (100 g, 0.42 mol) in tetrahydrofuran (2 L) was added palladium on carbon (10%, 10 g). The mixture was stirred under an atmosphere of hydrogen for 12 hours. The catalyst was removed by filtration and the filtrate was evaporated to afford the product 2-methoxy-4-morpholinoaniline (87 g, yield 100%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f7c1c8ff161548b0b291edacacdca48b
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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