Ethyl cyanoacetate → HCID 2842211, compound

HRID 1953845Notes

Reaction equation

HRID 1953845 reaction equation
[K].[C:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:3].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1>C(O)(C)(C)C>[C:2]([CH:4]([C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:3]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 796132-Chloro-3-nitropyridineHCID 5462222Potassium2×

Product 1

HCID 2842211HCID 2842211, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

Potassium (2.5 g, 63 mmol) was carefully added in small lumps to dry t-butanol (80 mL, distilled from calcium hydride). Upon complete addition, the reaction was warmed to 50° and stirred until all the potassium was consumed. Ethyl cyanoacetate (6.71 mL, 63 mmol) was added and a thick white precipitate was formed. 2-Chloro-3-nitropyridine (5 g, 31.5 mmol) was added in hot (60° C.) t-butanol (80 mL) and the reaction turned dark orange upon addition. The reaction was heated to reflux for two hours, the t-butanol was removed and the residue partitioned between hydrochloric acid (1N) and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic phase was dried over magnesium sulfate, filtered and the solvent removed. The brown solid residue was recrystallized from ethyl acetate to give the desired product as red needles (4.8 g, 65%); m.p. 133-134° C.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction was warmed to 50°
  3. customwas consumed
  4. customa thick white precipitate was formed
  5. additionthe reaction turned dark orange upon addition
  6. temperatureThe reaction was heated
  7. temperatureto reflux for two hours
  8. customthe t-butanol was removed
  9. customthe residue partitioned between hydrochloric acid (1N) and ethyl acetate
  10. extractionThe aqueous phase was extracted with ethyl acetate
  11. dry with materialthe combined organic phase was dried over magnesium sulfate
  12. filtrationfiltered
  13. customthe solvent removed
  14. customThe brown solid residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-151fc4f1d2aa425087918c6e03097341
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

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