Morpholine → 3-Methoxy-5-morpholin-4-yl-2-nitro-phenol

HRID 515198Notes

Reaction equation

HRID 515198 reaction equation
F[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>CS(C)=O.O>[CH3:13][O:12][C:4]1[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=[C:2]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 184333835-Fluoro-3-methoxy-2-nitrophenol

Product 1

HCID 866997623-Methoxy-5-morpholin-4-yl-2-nitro-phenolYield 26.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 5-fluoro-3-methoxy-2-nitro-phenol (2.0 g, 10.6 mmol) in dimethylsulfoxide (25 ml) is added morpholine (9.2 ml, 106 mmol) at room temperature. The resulting mixture is heated at 100° C. for 2 h. After completion of reaction (monitored by TLC), the mixture is diluted with water (40 ml) and the aqueous layer is extracted with ethyl acetate (3×30 ml). The combined organic layers are washed with water (30 ml), brine (20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product is purified by flash column chromatography (45% ethyl acetate/hexane) to yield 3-methoxy-5-morpholin-4-yl-2-nitro-phenol (0.71 g, 2.78 mmol, 26%).

Workup

  1. customAfter completion of reaction (monitored by TLC)
  2. extractionthe aqueous layer is extracted with ethyl acetate (3×30 ml)
  3. washThe combined organic layers are washed with water (30 ml), brine (20 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash column chromatography (45% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-01f60f7af3c4405fbeba30e8428e32f6
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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