Morpholine → 5-Morpholino-2-nitrophenol

HRID 1041650Notes

Reaction equation

HRID 1041650 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C(#N)C.O>[N:12]1([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 99375-Fluoro-2-nitrophenol

Product 1

HCID 27993995-Morpholino-2-nitrophenolYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

5-Fluoro-2-nitro-phenol (3.05 g, 19.4 mmol; Alfa Aesar) in Acetonitrile (20 mL) was treated with Morpholine (3.6 mL, 41 mmol) under an atmosphere of Nitrogen. After 40 h at rt, the mixture was heated at 50° C. for 6 h to drive to completion. The mixture was concentrated to ca. ½ volume, precipitate formed and the mixture was diluted with 100 mL water. The solids were collected and washed 2×50 mL water then dried to afford 5-Morpholin-4-yl-2-nitro-phenol as a yellow solid (3.77 g, 87%). 1H-NMR (DMSO): 7.88 (d, 1H, J=9.6 Hz), 6.64 (dd, 1H, J=2.4, 9.6 Hz), 6.43 (d, 1H, J=2.4 Hz), 3.70 (t, 4H, J=4.8 Hz), 3.41 (t, 4H, J=4.8 Hz).

Workup

  1. concentrationThe mixture was concentrated
  2. customformed
  3. customThe solids were collected
  4. washwashed 2×50 mL water
  5. customthen dried

Sources & evidence

ORD record
ord-134540aa65544a3083837aa51be80a13
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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