2-(Methylamino)ethanol → Ethanol, 2-(methyl-4-pyridinylamino)-

HRID 901735Notes

Reaction equation

HRID 901735 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:9][NH:10][CH2:11][CH2:12][OH:13]>C(=O)(O)[O-].[Na+]>[CH3:9][N:10]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 10419367Ethanol, 2-(methyl-4-pyridinylamino)-

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-chloropyridine hydrochloride salt (15.0 g) and 2-methylaminoethanol (30 mL) was refluxed for 48 hour. After cooling to rt the crude mixture was added slowly to saturated solution of sodium bicarbonate (150 mL). The product was extracted with EtOAc (3×100 mL), the combined EtOAc was washed with brine (50 mL), dried (Na2SO4) and removed in vacuo to give the desired product 2-[methyl(pyridin-4-yl)amino]ethanol as yellow solid (7.0 g).

Workup

  1. temperaturewas refluxed for 48 hour
  2. extractionThe product was extracted with EtOAc (3×100 mL)
  3. washthe combined EtOAc was washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-e53bdd103a0e4d239d8a35eefd926979
Source dataset
uspto-grants-2008_04
Patent number
US07361678B2

Reaction notes

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