2-Pyridinamine, 5-bromo-6-methyl- → 6-Amino-2-methylpyridine-3-carbonitrile

HRID 377212Notes

Reaction equation

HRID 377212 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5](Br)=[CH:4][CH:3]=1.[Cu][C:11]#[N:12]>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]#[N:12])=[C:6]([CH3:8])[N:7]=1

Participants

4

Reactant 2

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 178418546HCID 178418546, compound

Product 1

HCID 27946626-Amino-2-methylpyridine-3-carbonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-amino-3-bromo-2-methyl-pyridine (20 g, 0.107 mol) and copper (I) cyanide (11.0 g, 0.123 mol) in DMF (25 mL) was heated to reflux for 4 h. The DMF was evaporated in vacuo and the residue was partitioned between ethyl acetate and 10% sodium cyanide solution. The organic layer was washed with 10% sodium cyanide solution and brine, dried (Na2SO4) and evaporate in vacuo to a brown solid. This was dissolved in a minimum amount of ethyl acetate and the product was precipitated by adding hexane. The mixture was filtered to give the title compound (12 g, 85%) as a brown powder:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe DMF was evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate and 10% sodium cyanide solution
  5. washThe organic layer was washed with 10% sodium cyanide solution and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporate in vacuo to a brown solid
  8. dissolutionThis was dissolved in a minimum amount of ethyl acetate
  9. customthe product was precipitated
  10. additionby adding hexane
  11. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-7d1fa5385c194c2f8bf9af340aebe61c
Source dataset
uspto-grants-2000_02
Patent number
US06025372

Reaction notes

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