Morpholine → (2-Fluoro-3-methoxy-4-nitrophenyl)(morpholino)methanone

HRID 2406317Notes

Reaction equation

HRID 2406317 reaction equation
[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][C:3]=1[C:4]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:6]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579556232-Fluoro-3-methoxy-4-nitrobenzoic acid

Product 1

HCID 70099135(2-Fluoro-3-methoxy-4-nitrophenyl)(morpholino)methanoneYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-fluoro-3-methoxy-4-nitrobenzoic acid (180 mg, 0.97 mmol) in DCM (8 mL) was added morpholine (0.17 mL. 1.9 mmol), DIEA (0.25 mL) and HBTU (0.4 g, 1.05 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was then diluted with water and extracted with DCM (3×). The combined extracts were washed with water, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography to give (2-fluoro-3-methoxy-4-nitrophenyl)(morpholino)methanone (0.20 g, 83%).

Workup

  1. extractionextracted with DCM (3×)
  2. washThe combined extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-e3d007e88b00449f92986a93fb44b827
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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