3-Cyanopyridine → 6-Tert-butylpyridine-3-carbonitrile

HRID 1181386Notes

Reaction equation

HRID 1181386 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:9][C:10](C)([CH3:14])[C:11](O)=O.[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O.[NH4+].[OH-]>S(=O)(=O)(O)O.O.[N+]([O-])([O-])=O.[Ag+]>[C:10]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][N:5]=1)([CH3:14])([CH3:11])[CH3:9]

Participants

8

Reactant 4

HCID 793-CyanopyridineHCID 6417Pivalic acidHCID 14923Ammonium HydroxideHCID 62648Ammonium Persulfate

Product 1

HCID 194251856-Tert-butylpyridine-3-carbonitrileYield 101.4%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-cyanopyridine (10 g, 96 mmol), trimethylacetic acid (9.8 g, 96 mmol) and silver nitrate (1.63 g, 9.6 mmol) in 10% aqueous sulfuric acid (100 ml) at 70° C. was added dropwise a solution of ammonium peroxodisulfate (21.9 g, 96 mmol) in water (120 ml). After complete addition the mixture was stirred at 70° C. for 2 hours. The mixture was cooled and basified by the addition of 33% aqueous NH4OH, and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (100 ml), dried (Na2SO4) and evaporated to give the title compound (15.6 g, 100%).

Workup

  1. additionAfter complete addition the mixture
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic layers were washed with brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-bc407098f6474e07a5aa5c887b58f67b
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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