Acetic Acid → Ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate

HRID 751611Notes

Reaction equation

HRID 751611 reaction equation
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[Cl:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1.C(O)(=O)C>C(OCC)C.C(O)C.O>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:22][C:20]1[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=[C:16]([Cl:15])[CH:21]=1)[CH3:14]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 23670592Potassium ethoxide

Product 1

HCID 53472030Ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Route A: To a solution of potassium ethoxide (1.46 g, 17.4 mmol) in diethyl ether (80 mL) and ethanol (10 mL) under an argon atmosphere was added diethyl oxalate (2.4 mL, 17.4 mmol) and the mixture stirred at rt for 0.5 h. A solution of 2-chloro-4-methyl-5-nitropyridine (3.0 g, 17.4 mmol) in diethyl ether (20 mL) was added resulting in the formation of a dark green precipitate. The reaction was stirred at rt for 15 h, cooled to 0° C., filtered and washed with cold diethyl ether to give a dark green solid. The solid was dissolved in water (200 mL) and acidified to pH 4 with acetic acid to give an orange precipitate. The solid was collected by filtration and dried to give the title compound. m/z (ES+)=273 [M+H]+.

Workup

  1. customresulting in the formation of a dark green precipitate
  2. stirringThe reaction was stirred at rt for 15 h
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. washwashed with cold diethyl ether
  6. customto give a dark green solid
  7. customto give an orange precipitate
  8. filtrationThe solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-650b7c954fa54154881a7e881dfa8813
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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