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

HRID 553565Notes

Reaction equation

HRID 553565 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[H][H].Cl[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][N:12]=1>O>[CH3:3][O:4][CH2:5][CH2:6][O:7][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 percent strength sodium hydride suspension was introduced into 10 ml of ethylene glycol monomethyl ether, and the mixture was stirred until the evolution of hydrogen had ceased. 516 mg of 2-chloro-4-methyl-5-nitropyridine are added, and the mixture is stirred at room temperature until the reaction has gone to completion. 20 ml of water are added, and the mixture is extracted with methyl tert-butyl ether. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:3). This gives 2-(2-methoxyethoxy)-4-methyl-5-nitropyridine as a colorless oil. C9H12N2O4 (212.21), MS (ESI): 213 (M+H+).

Workup

  1. extractionthe mixture is extracted with methyl tert-butyl ether
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=1:3)

Sources & evidence

ORD record
ord-b25e10aa9eeb4f3dade267c8d82dd6a5
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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