2-(Methylamino)ethanol → HCID 19418837, compound

HRID 2395755Notes

Reaction equation

HRID 2395755 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanol2×HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 19418837HCID 19418837, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(Methylamino)ethanol (3.04 ml) is added to a mixture of 2-chloro-3-nitropyridine (3.00 g) and of potassium carbonate (5.22 g) in acetonitrile (90 ml) at 0°. The mixture is stirred for 2.5 hr at 20°-25° and additional 2-(methylamino)ethanol (1.5 ml) is added. The mixture is stirred for 1.5 hr, concentrated to a gum and diluted with methylene chloride (85 ml) and water (20 ml). The layers are separated and the organic phase is washed in water and dried over magnesium sulfate. Removal of solvent under reduced pressure gives the title compound, NMR (CDCl3) 8.27, 8.14, 6.76, 4.38, 3.88 and 2.87 δ.

Workup

  1. stirringThe mixture is stirred for 1.5 hr
  2. concentrationconcentrated to a gum
  3. additiondiluted with methylene chloride (85 ml) and water (20 ml)
  4. customThe layers are separated
  5. washthe organic phase is washed in water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-7d14b03ac44045a08155cf89a07ee7f1
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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