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

HRID 345438Notes

Reaction equation

HRID 345438 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+]>C(O)CC(C)C>[CH3:9][N:10]([CH2:11][CH2:12][OH:13])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 10419367Ethanol, 2-(methyl-4-pyridinylamino)-Yield 18.6%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 4-chloropyridine hydrochloride (4.50 g), 2-(methylamino)ethanol (2.25 g) and sodium bicarbonate (7.56 g) in isoamyl alcohol (50 ml) was heated under reflux for 70 hours and then evaporated. The residue was extracted several times with hot ethyl acetate and the combined extracts were filtered and evaporated until crystallisation commenced. The solution was allowed to cool and the solid was filtered off to give the title compound, (0.85 g), m.p. 90°-91°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 70 hours
  3. customevaporated
  4. extractionThe residue was extracted several times with hot ethyl acetate
  5. filtrationthe combined extracts were filtered
  6. customevaporated until crystallisation
  7. temperatureto cool
  8. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-0746f4a606234a3a9a6703546c82ccb1
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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