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

HRID 1487188Notes

Reaction equation

HRID 1487188 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+]>CS(C)=O>[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

5

Reactant 3

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

Product 1

HCID 81388Morpholine, 4-(3-methoxy-4-nitrophenyl)-Yield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (100 g, 0.584 mol) and morpholine (60 g, 0.689 mol) in dimethyl sulfoxide (60 mL) was added potassium carbonate (120 g, 0.870 mol). The mixture was stirred at 70° C. for 6 hours, and then poured into ice-water. The precipitate was collected by filtration and washed by water, dried to afford the product 4-(3-methoxy-4-nitrophenyl)morpholine (100 g, yield 72%).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed by water
  3. customdried

Sources & evidence

ORD record
ord-917241fe979447468d024feb4c4f63c3
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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