Water → Morpholine, 4-(3-methoxy-4-nitrophenyl)-

HRID 1887688Notes

Reaction equation

HRID 1887688 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 81388Morpholine, 4-(3-methoxy-4-nitrophenyl)-Yield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (24.4 g, 0.14 mol) in 200 mL DMF was added morpholine (25.7 mL, 0.28 mol), followed by the addition of K2CO3 (23.6 g, 0.17 mol). The mixture was stirred at room temperature for 48 h. The mixture was poured into 0.7 L H2O and the precipitate was collected by filtration. The precipitate was further rinsed with 0.5 L H2O. The resulting solid was air dried by purging with a flow of air for 24 h, thus affording 29.3 g of 4-(3-methoxy-4-nitrophenyl)morpholine (0.12 mol, 86%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washThe precipitate was further rinsed with 0.5 L H2O
  3. customdried
  4. customby purging with a flow of air for 24 h

Sources & evidence

ORD record
ord-19c5fd3e14f24888aaf6a2775b77539e
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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