Sodium Cyanide → 6-Amino-4-methylnicotinonitrile

HRID 1740948

Reaction equation

HRID 1740948 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5](Br)=[CH:4][N:3]=1.[Cu][C:11]#[N:12].[C-]#N.[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:11]#[N:12])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 8176952-Amino-5-bromo-4-methylpyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 99641036-Amino-4-methylnicotinonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-5-bromo-4-methylpyridine (4.0 g, 21.4 mmol) and copper(I) cyanide (2.2 g, 24.6 mmol) in N,N-dimethylformamide (5 mL) was stirred for 4 h at reflux temperature. The hot mixture was poured into a warm solution of sodium cyanide (4.3 g) in water (13 mL). After the mixture was vigorously shaken, the mixture was extracted with ethyl acetate. The organic extract was washed with 10% aqueous sodium cyanide, saturated brine solution and evaporated. The title compound was obtained as a solid after chromatography on silica gel (15% acetone/hexane); yield 1.81 g (64%).

Workup

  1. temperatureat reflux temperature
  2. stirringAfter the mixture was vigorously shaken
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with 10% aqueous sodium cyanide, saturated brine solution
  6. customevaporated

Sources & evidence

ORD record
ord-91262695ff1a4c09be98dce544f04b85
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Linked notes

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