2-(Methylamino)ethanol → HCID 18998890, compound

HRID 2260712Notes

Reaction equation

HRID 2260712 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10]C)=O.[H-].[Na+].F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.[CH3:23][NH:24][CH2:25][CH2:26][OH:27]>CN(C)C=O.O>[CH3:23][N:24]([CH2:25][CH2:26][O:27][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1)[C:8](=[O:10])[CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

7

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 74264Methyl 2-pyridylacetate

Product 1

HCID 18998890HCID 18998890, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-pyridylacetate (10.0 g, 8.9 ml) was dissolved in 2-(N-methylamino)ethanol (150 ml) and the mixture heated at reflux for 84 hours, then cooled and concentrated under reduced pressure. The residue was dissolved in water (100 ml)and continuously extracted overnight with ethyl acetate. The ethyl acetate solution was dried (MgSO4) and evaporated to afford an oil which no longer displayed an ester signal (δ3.70) in the nmr spectrum. The oil was dissolved in dry dimethylformamide (150 ml) at room temperature under a nitrogen atmosphere, and sodium hydride (60% dispersion in oil, 3.42 g) was added. The mixture was stirred for 1 hour, then 4-fluorobenzaldehyde (10.6 g, 9.2 ml) was added and the mixture heated at 80° C. for 22.5 hours, cooled, diluted with water (1 l) and extracted with ethyl acetate (3×400 ml). The combined ethyl acetate layers were washed with water (3×1 l) and brine (1 l), dried (MgSO4) and evaporated. The resulting oil was triturated with hexane and the residue chromatographed on silica gel with 1.5% methanol in dichloromethane as solvent to afford the title compound as an oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 84 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in water (100 ml)and continuously extracted overnight with ethyl acetate
  6. dry with materialThe ethyl acetate solution was dried (MgSO4)
  7. customevaporated
  8. customto afford an oil which
  9. temperaturecooled
  10. extractionextracted with ethyl acetate (3×400 ml)
  11. washThe combined ethyl acetate layers were washed with water (3×1 l) and brine (1 l)
  12. dry with materialdried (MgSO4)
  13. customevaporated
  14. customThe resulting oil was triturated with hexane
  15. customthe residue chromatographed on silica gel with 1.5% methanol in dichloromethane as solvent

Sources & evidence

ORD record
ord-a44ad749483946368fe8a151cf56a97d
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Reaction notes

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