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

HRID 1595215Notes

Reaction equation

HRID 1595215 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 heated at reflux for 10 hours and then cooled to 80° C. and poured into a solution of sodium cyanide (40 mmol) in water. After stirring for one hour at ambient temperature, the mixture is extracted with ethyl acetate. The organic phase is washed and then dried and evaporated to yield the expected product in the form of an ochre solid.

Workup

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

Sources & evidence

ORD record
ord-6ab589e79d69487bae9f8e0512f9feac
Source dataset
uspto-grants-2001_09
Patent number
US06288077B1

Reaction notes

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