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

HRID 2214399Notes

Reaction equation

HRID 2214399 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

First, 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., and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 3.3 g of 2-{1-(methoxycarbonyl)ethoxy}-3-nitropyridine.

Workup

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

Sources & evidence

ORD record
ord-8f43efbcd68244ebb0eb27f98ddf9153
Source dataset
uspto-grants-2006_09
Patent number
US07109148B2

Reaction notes

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