Water → 2-(2-Methoxyethoxy)-4-methyl-5-nitropyridine

HRID 2250437Notes

Reaction equation

HRID 2250437 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=1.O>COC(C)(C)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 598200212-(2-Methoxyethoxy)-4-methyl-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To 20 mL of 2-Methoxy-ethanol 243 mg of NaH (6.09 mmol, 60% suspension in oil) were added and the mixture was stirred for 15 min. in an argon atmosphere. 1 g (5.8 mmol) 2-Chloro-4-methyl-5-nitro-pyridine were added and the reaction mixture was stirred for 3 h at room temperature. After addition of 40 mL water and methyl-tertbutyl ether, the phases were separated and the organic phase was washed with saturated NaHCO3 solution and water and was dried over Na2SO4. After filtration, the solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel using heptane/ethyl acetate=8/2. 2-(2-Methoxy-ethoxy)-4-methyl-5-nitro-pyridine was isolated as colourless oil. Yield: 0.73 g.

Workup

  1. stirringthe reaction mixture was stirred for 3 h at room temperature
  2. customthe phases were separated
  3. washthe organic phase was washed with saturated NaHCO3 solution and water
  4. dry with materialwas dried over Na2SO4
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-cf8f083762c14792879dff4f171f3097
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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