Sodium Cyanide → 6-Amino-2-methylpyridine-3-carbonitrile

HRID 650925Notes

Reaction equation

HRID 650925 reaction equation
[Cu][C:2]#[N:3].[NH2:4][C:5]1[N:10]=[C:9]([CH3:11])[C:8](Br)=[CH:7][CH:6]=1.[C-]#N.[Na+]>CN(C)C=O.O>[NH2:4][C:5]1[N:10]=[C:9]([CH3:11])[C:8]([C:2]#[N:3])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 178418546HCID 178418546, compound

Product 1

HCID 27946626-Amino-2-methylpyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Copper(I) cyanide (12 mmol) is added to 10 mmol of 6-amino-3-bromo-2-methylpyridine dissolved in dimethylformamide. The mixture is refluxed for 10 hours, and then cooled to 80° C. and poured into a solution of sodium cyanide (40 mmol) in water. After stirring for 1 hour at room temperature, the mixture is extracted with ethyl acetate. The organic phase is washed, then dried and evaporated to yield the expected product in the form of an ochre solid.

Workup

  1. temperatureThe mixture is refluxed for 10 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic phase is washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-55a82148e20a460a8a3bf861d4ed35da
Source dataset
uspto-grants-2001_08
Patent number
US06277851B1

Reaction notes

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