2-(Dimethylamino)ethanol → 908117-05-5

HRID 912100Notes

Reaction equation

HRID 912100 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:8])[CH2:5][CH2:6][OH:7].[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12](Cl)[CH:11]=1>C1(C)C=CC=CC=1>[CH3:3][N:4]([CH3:8])[CH2:5][CH2:6][O:7][C:12]1[CH:11]=[C:10]([NH2:9])[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 844322-Chloropyridin-4-amine

Product 1

HCID 59244595908117-05-5Yield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (159 mg, 60% mineral oil dispersion, 3.98 mmol) was placed in a dried flask under a nitrogen atmosphere, followed by sequential addition of anhydrous toluene (10 ml) and 2-dimethylaminoethanol (177 mg, 2.0 mmol) with a syringe. After the resulting mixture was stirred at room temperature for 40 minutes, 4-amino-2-chloropyridine (203 mg, 1.59 mmol) was added, followed by heating to reflux for 16 hours. The reaction mixture was cooled, which was subsequently added dropwise slowly onto ice water, followed by extraction twice with ethyl acetate (10 ml). The organic layer was washed with brine (10 ml), and dried over sodium sulfate, followed by distilling off under reduced pressure, to obtain a crude product as a pale brown solid (180 mg).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. additionwhich was subsequently added dropwise slowly onto ice water
  5. extractionfollowed by extraction twice with ethyl acetate (10 ml)
  6. washThe organic layer was washed with brine (10 ml)
  7. dry with materialdried over sodium sulfate
  8. distillationby distilling off under reduced pressure

Sources & evidence

ORD record
ord-257062406f7348df8796ea81175b7fe6
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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