Diethyl Oxalate → Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

HRID 550894Notes

Reaction equation

HRID 550894 reaction equation
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[CH3:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>C(O)C>[N+:19]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:13]=1[CH2:12][C:3](=[O:5])[C:2]([O:9][CH2:10][CH3:11])=[O:8])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 5218284-Methyl-3-nitropyridineHCID 5360545Sodium

Product 1

HCID 23269548Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 930 mg of sodium in 50 mL of absolute ethanol are rapidly added 26 mL of diethyl oxalate. The reaction medium is stirred for 15 minutes at 20° C. A solution of 3.8 g of 4-methyl-3-nitropyridine in 50 mL of absolute ethanol is then added dropwise over 1 hour. The reaction medium is stirred for 4 hours at a temperature in the region of 20° C. and then concentrated under reduced pressure. The residue is taken up in 100 mL of ethyl ether and then filtered. The solid is stirred with 40 mL of 5N hydrochloric acid and then filtered, washed with water and dried under vacuum at 40° C. to give 6.2 g of ethyl 3-(3-nitro-4-pyridyl)-2-oxopropionate having the following characteristics:

Workup

  1. stirringThe reaction medium is stirred for 4 hours at a temperature in the region of 20° C.
  2. concentrationconcentrated under reduced pressure
  3. filtrationfiltered
  4. stirringThe solid is stirred with 40 mL of 5N hydrochloric acid
  5. filtrationfiltered
  6. washwashed with water
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-1a64d812e44e4c1fb937939e0611cd98
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Reaction notes

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