Ethylene Glycol → HCID 19418834, compound

HRID 864403Notes

Reaction equation

HRID 864403 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].Cl[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1>O>[OH:5][CH2:4][CH2:3][O:6][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydride2×HCID 796132-Chloro-3-nitropyridine

Product 1

HCID 19418834HCID 19418834, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride in oil (60%, 131 mg) is added to ethylene glycol (6.0 ml) and 2-chloro-3-nitropyridine (430 mg) is added. The mixture is stirred for 26 hours during which time additional sodium hydride in oil (60%, 100 mg) is added. Water is added, the pH is adjusted to 9 and the solution is extracted with methylene chloride (3×50 ml). The combined organic layers are dried with saline and sodium sulfate and concentrated. Chromatography on silica gel with a methanol/chloroform gradient affords the title compound, Rf =0.32 (TLC on silica gel, ethyl acetate/hexane [50/50]).

Workup

  1. additionis added
  2. additionis added
  3. extractionthe solution is extracted with methylene chloride (3×50 ml)
  4. dry with materialThe combined organic layers are dried with saline and sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-564bd2d7b413435ca28d70540e61d785
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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