Diethyl Oxalate → Ethyl 3-(6-methoxy-3-nitropyridin-2-yl)-2-oxopropanoate

HRID 1799571Notes

Reaction equation

HRID 1799571 reaction equation
[K].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[CH3:12][O:13][C:14]1[N:19]=[C:18]([CH3:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=1>C(O)C>[CH3:12][O:13][C:14]1[N:19]=[C:18]([CH2:20][C:3](=[O:5])[C:2]([O:9][CH2:10][CH3:11])=[O:8])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2304756-Methoxy-2-methyl-3-nitropyridineHCID 5462222Potassium2×

Product 1

HCID 59753655Ethyl 3-(6-methoxy-3-nitropyridin-2-yl)-2-oxopropanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A roundbottom flask was charged with ethanol (540 ml) and (7.2 L). To this was added potassium (81.6 g, 2.09 mol) and mixture was stirred until all the potassium dissolved. Diethyl oxalate (306 g, 2.10 mol) was then added. The mixture was stirred for 5 minutes and then 6-methoxy-2-methyl-3-nitropyridine (320.0 g, 1.87 mol) was added. The resulting solution was stirred at room temperature for 36 hours. The slurry was filtered and the collected solids were washed thoroughly with ether and dried under reduced pressure. The solid was then suspended in 30 ml of water acetic acid was added until the pH=4. The solids that formed were collected by filtration to afford the title compound.

Workup

  1. dissolutiondissolved
  2. stirringThe resulting solution was stirred at room temperature for 36 hours
  3. filtrationThe slurry was filtered
  4. washthe collected solids were washed thoroughly with ether
  5. customdried under reduced pressure
  6. additionwas added until the pH=4
  7. customThe solids that formed
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7f283420907e42fdabb4b995861cad5b
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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