Methyl Lactate → 2-{1-(Methoxycarbonyl)ethoxy}-3-nitropyridine

HRID 1862260Notes

Reaction equation

HRID 1862260 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:18][CH3:19])(=[O:17])[CH:14]([CH3:16])[OH:15]>O1CCOCC1>[CH3:19][O:18][C:13]([CH:14]([O:15][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:16])=[O:17]

Participants

5

Reactant 3

HCID 11040Methyl LactateHCID 24758Sodium hydrideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 219335712-{1-(Methoxycarbonyl)ethoxy}-3-nitropyridineYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.8 g of sodium hydride was added to a mixture of 3.17 g of 2-chloro-3-nitropyridine, 2.19 g of methyl lactate and 20 ml of 1,4-dioxane at 10° C. The mixture was stirred at room temperature for 1.5 hours, then, 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 3.3 g of 2-{1-(methoxycarbonyl)ethoxy}-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-8c35a9af41644d81880d7f86246997aa
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

Loading…