Methanol → 4-(Methylamino)benzonitrile

HRID 967777Notes

Reaction equation

HRID 967777 reaction equation
CO.[CH3:3][NH2:4].CO.F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1>O>[CH3:3][NH:4][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 145174-FluorobenzonitrileHCID 57454252Monomethylamine methanol

Product 1

HCID 109645514-(Methylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 40% methylamine methanol solution (7.5 mL) was added to a methanol (2.5 mL) solution of 4-fluorobenzonitrile (2.00 g) and the mixture was heated under reflux for fifteen hours under nitrogen atmosphere. After the solvent was removed under reduced pressure, to the residue obtained was added water (15 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous sodium sulfate. The oil obtained by removal of the solvent under reduced pressure was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1) to obtain the titled compound (0.48 g) as crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for fifteen hours under nitrogen atmosphere
  3. customAfter the solvent was removed under reduced pressure, to the residue
  4. customobtained
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine successively
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe oil obtained by removal of the solvent under reduced pressure
  9. customwas purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-62cfe17011184c56aeadebd041802859
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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