2-Chloro-4,6-dimethyl-3-pyridinecarbonitrile → 4,6-Dimethylnicotinonitrile

HRID 399623Notes

Reaction equation

HRID 399623 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([CH3:11])[N:3]=1.[Sn]>Cl.O>[C:8]([C:7]1[C:6]([CH3:10])=[CH:5][C:4]([CH3:11])=[N:3][CH:2]=1)#[N:9]

Participants

5

Reactant 2

HCID 2232612-Chloro-4,6-dimethyl-3-pyridinecarbonitrileHCID 5352426Tin atom

Product 1

HCID 2439174,6-DimethylnicotinonitrileYield 54%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

23 g of 2-chloro-3-cyano-4,6-dimethylpyridine are dissolved in 185 ml of concentrated hydrochloric acid and 240 ml of water. 25.4 g of tin metal are added and the mixture is brought to 100° C. The reaction is monitored by thin layer chromatography (TLC). When the reaction is complete, the mixture is allowed to return to room temperature and filtered and the filtrate is neutralized using sodium hydroxide solution. The mixture is extracted with methylene chloride and the combined organic phases are washed with saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulphate. The solution is concentrated to give 5-cyano-2,4-dimethyl-pyridine in the form of a yellow precipitate.

Workup

  1. customis brought to 100° C
  2. customto return to room temperature
  3. filtrationfiltered
  4. extractionThe mixture is extracted with methylene chloride
  5. washthe combined organic phases are washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-51804f6f471e4dfb910e9c186bc95b92
Source dataset
uspto-grants-1998_10
Patent number
US05821255

Reaction notes

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