Morpholine → 5-Morpholino-2-nitroaniline

HRID 1882890Notes

Reaction equation

HRID 1882890 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CN1C(=O)CCC1.O>[N:12]1([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 753995-Fluoro-2-nitroaniline

Product 1

HCID 5967255-Morpholino-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

5-Fluoro-2-nitrophenylamine (1.0 eq) and morpholine (3.0 eq) were dissolved in NMP and heated at 100° C. for 1 hour. The solution was cooled to room temperature and diluted with water. The resulting precipitate was filtered and dried under vacuum to yield 5-morpholin-4-yl-2-nitrophenylamine. The resulting solid was recrystallized from EtOH to afford pure product as a bright yellow solid. LC/MS m/z 224.1 (MH+), Rt 1.89 minutes.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0b915b90825d4b979c7a601eb80bd57d
Source dataset
uspto-grants-2004_07
Patent number
US06759417B2

Reaction notes

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