2-(Methylamino)ethanol → HCID 19418837, compound

HRID 864401Notes

Reaction equation

HRID 864401 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 with 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 2.87δ.

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 with water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-ea04daf535504efba1144fa4574c8a5d
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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