3-Cyanopyridine → HCID 21075124, compound

HRID 576055Notes

Reaction equation

HRID 576055 reaction equation
[C:1](O)(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[C:8]([C:10]1C=N[CH:13]=[CH:14][CH:15]=1)#[N:9].[NH4+:16].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O>O.C(OCC)(=O)C.[N+]([O-])([O-])=O.[Ag+]>[C:2]([C:1]1[N:16]=[C:10]([C:8]#[N:9])[CH:15]=[CH:14][CH:13]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 793-CyanopyridineHCID 6417Pivalic acidHCID 62648Ammonium Persulfate

Product 1

HCID 21075124HCID 21075124, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Silver nitrate (4.43 g, 28.8 mmol) was added to a suspension of pivalic acid (1.96 g, 19.2 mmol), 3-cyanopyridine (2.00 g, 19.2 mmol) and ammonium peroxodisulfate (6.58 g, 28.8 mmol) in water (40 mL). The mixture was stirred at room temperature for 10 min and then stirred at an external temperature of 80° C. for 2 hr. After cooling, the reaction mixture was diluted with ethyl acetate and the resulting insoluble matter was removed by filtration through Celite (registered trademark). The aqueous layer was separated from the filtrate, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=4:1) to afford 6-tert-butylpyridine-2-carbonitrile as a yellow oil (2.71 g).

Workup

  1. stirringstirred at an external temperature of 80° C. for 2 hr
  2. temperatureAfter cooling
  3. customthe resulting insoluble matter was removed by filtration through Celite (registered trademark)
  4. customThe aqueous layer was separated from the filtrate
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

Sources & evidence

ORD record
ord-291ff228fa4a45978d4ad033d6590d79
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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