Sodium Cyanide → 1,5-dicyanonaphthalene

HRID 1824343Notes

Reaction equation

HRID 1824343 reaction equation
I[C:2]1[C:11]2[C:6](=[C:7](I)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:13]([Cu])#[N:14].[C-:16]#[N:17].[Na+]>CN(C=O)C>[C:2]1([C:13]#[N:14])[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:16]#[N:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 38021551,5-diiodonaphthaleneHCID 178418546HCID 178418546, compound

Product 1

HCID 114580091,5-dicyanonaphthaleneYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,5-Diiodonaphthalene (8.4 g) was reacted with a mixture of 4.2 g CuCN and 40 ml DMF under reflux conditions overnight. The mixture was cooled and poured into 120 ml aqueous solution containing 12.6 g NaCN. The mixture was stirred for four hours and the filtered product was repeatedly washed with copious amounts of water and dried. The isolated crude product (3.6 g, 92% yield, m.pt., 258–260° C.) was recrystallized from toluene to yield 3.2 g of the product (81% yield, m.pt., 260–262° C.).

Workup

  1. temperatureThe mixture was cooled
  2. washthe filtered product was repeatedly washed with copious amounts of water
  3. customdried
  4. customThe isolated crude product (3.6 g, 92% yield, m.pt., 258–260° C.)
  5. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-86ba34d3a50740cb85c8eac6835ee14c
Source dataset
uspto-grants-2006_05
Patent number
US07041779B1

Reaction notes

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