2-(Methylamino)ethanol → HCID 50851101, compound

HRID 1398085Notes

Reaction equation

HRID 1398085 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:4].[CH3:15][NH:16][CH2:17][CH2:18][OH:19].C(OCC)(=O)C>C(O)C>[OH:19][CH2:18][CH2:17][N:16]([CH3:15])[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8857Ethyl AcetateHCID 140220Acetanilide, 2-chloro-4'-nitro-

Product 1

HCID 50851101HCID 50851101, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2.946 g (13.73 mmol) of 2-chloro-N-(4-nitrophenyl)acetamide in 30 mL of ethanol was added 3.31 mL (41.18 mmol) of 2-(methylamino)ethanol and the mixture was refluxed for 4 hours. After the reaction mixture was cooled to room temperature and condensed, then, the residue was treated with ethyl acetate. The organic layer was washed with water and dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=40/1) to give 2.05 g (59%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customcondensed
  3. washThe organic layer was washed with water
  4. dry with materialdried over with anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=40/1)

Sources & evidence

ORD record
ord-45f0c4af4b924c218cb2b195f7bb0b48
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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