3-Cyanopyridine → HCID 69845219, compound

HRID 1384261Notes

Reaction equation

HRID 1384261 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.BrCC(OCC)=O.[Zn]>[NH2:2][C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 3

HCID 793-CyanopyridineHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 69845219HCID 69845219, compoundYield 78.4%

Reagents, catalysts & solvents 3

HCID 7748Ethyl bromoacetateCatalystHCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In an atmosphere of argon, activated zinc powder (4.88 g, 0.07 g atom) was suspended in anhydrous tetrahydrofuran (THF) (25.0 ml) to which was subsequently added dropwise several drops of ethyl bromoacetate while heating under reflux. When color of the reaction solution became green, 3-cyanopyridine (1.59 g, 15.0 mmol) was added to the solution, ethyl bromoacetate (6.0 ml, 51.4 mmol) was added dropwise thereto spending 50 minutes and then the mixture was heated under reflux for 15 minutes. After cooling, the reaction solution was diluted with THF, mixed with 50% potassium carbonate aqueous solution (15.0 ml) and then stirred for 30 minutes. After standing, the organic layer was collected and extracted three times with THF in the same manner and then the thus obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1-4:1) to obtain the title compound (2.26 g, 72.3%) as pale yellow oil.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. additionwas added dropwise
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 15 minutes
  6. temperatureAfter cooling
  7. customthe organic layer was collected
  8. extractionextracted three times with THF in the same manner
  9. dry with materialthe thus obtained organic layer was dried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:1-4:1)

Sources & evidence

ORD record
ord-fe9423c5ecbf4580be36b03272755acb
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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