2-(Methylamino)ethanol → HCID 50851101, compound

HRID 2079598Notes

Reaction equation

HRID 2079598 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-cc543cba4213474d84c37fc4ccbe3b31
Source dataset
uspto-grants-2011_04
Patent number
US07932250B2

Reaction notes

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