2-Amino-6-chloropyridine-3,5-dicarbonitrile → 2-Aminopyridine-3,5-dicarbonitrile

HRID 842705

Reaction equation

HRID 842705 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]#[N:11])=[C:4](Cl)[N:3]=1>[Pd].O1CCOCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]#[N:11])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 2959012-Amino-6-chloropyridine-3,5-dicarbonitrile

Product 1

HCID 2959122-Aminopyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-6-chloro-3,5-dicyanopyridine (Synth. Comm. 1993, 2605, 15.0 g, 84 mmol) and 10% palladium on carbon (10.0 g) in dioxane (150 mL) was shaken on a Parr apparatus under hydrogen (55 psi) for 16 h. More catalyst (7.5 g) was added and after a further 4 h the reaction mixture was filtered through celite washing through with ethanol and evaporated in vacuo. The residue was partitioned between methylene chloride and 1 M HCl. The insoluble material was collected by filtration and dried to give the title compound. The methylene chloride layer was washed with brine, dried (Na2SO4) and evaporated in vacuo to give additional product:

Workup

  1. filtrationwas filtered through celite
  2. washwashing through with ethanol
  3. customevaporated in vacuo
  4. customThe residue was partitioned between methylene chloride and 1 M HCl
  5. filtrationThe insoluble material was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a57ce74854b24acfbc7930dae628fd29
Source dataset
uspto-grants-2002_04
Patent number
US06376499B1

Linked notes

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