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

HRID 1693352Notes

Reaction equation

HRID 1693352 reaction equation
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>C(OCC)C.C(O)C>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])[CH3:14]

Participants

6

Reactant 3

HCID 7268Diethyl OxalateHCID 5218284-Methyl-3-nitropyridineHCID 23670592Potassium ethoxide

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of potassium ethoxide (3.1 g, 36.2 mmol) in diethyl ether (70 mL) and ethanol (10 mL) under an argon atmosphere was added diethyl oxalate (4.9 mL, 36.2 mmol) and the reaction stirred at rt for 30 min. A solution of 4-methyl-3-nitropyridine (5.0 g, 36.2 mmol) in diethyl ether (20 mL) was added resulting in the immediate formation of a dark red precipitate. The reaction mixture was stirred at rt for 72 h, then cooled to 0° C. and filtered. The solid was dissolved in water (500 mL) acidified to pH 4 with acetic acid and the precipitate collected and dried to give the title compound as a red solid. δH (d6 DMSO): 1.27 (3H, t), 4.25 (2H, q), 6.74 (1H, s), 8.34 (1H, d), 8.43 (1H, d), 8.98 (1H, s); m/z (ES+)=239 [M+H]+.

Workup

  1. customresulting in the immediate formation of a dark red precipitate
  2. stirringThe reaction mixture was stirred at rt for 72 h
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in water (500 mL)
  6. customthe precipitate collected
  7. customdried

Sources & evidence

ORD record
ord-478fe2ca9e2e42b381fc2503cdd81988
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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