Sodium hydride → Methyl 2-(3-nitropyridin-2-yloxy)acetate

HRID 1862244Notes

Reaction equation

HRID 1862244 reaction equation
[H-].[Na+].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[C:13]([O:17][CH3:18])(=[O:16])[CH2:14][OH:15]>O1CCOCC1>[CH3:18][O:17][C:13]([CH2:14][O:15][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 12115511Methyl 2-(3-nitropyridin-2-yloxy)acetateYield 70.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.4 g of sodium hydride was added to a mixture of 1.59 g of 2-chloro-3-nitropyridine, 0.95 g of methyl glycolate and 10 ml of 1,4-dioxane at 10° C. The mixture was stirred at room temperature for 2 hours, then, the reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.5 g of 2-(methoxycarbonyl)methoxy-3-nitropyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-928703258bed4997b0ef2dcab2c5d316
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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