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

HRID 1362927Notes

Reaction equation

HRID 1362927 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

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 was stirred at rt for 30 min. 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 a 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 a precipitate
  8. filtrationThe solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-5c772868ecdf41978e5e3930f9d23390
Source dataset
uspto-grants-2011_02
Patent number
US07884112B2

Reaction notes

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