3-Hydroxypyridine → 4-(Pyridin-3-yloxy)-phthalonitrile

HRID 1618255Notes

Reaction equation

HRID 1618255 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:4]2[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=2)[C:8]#[N:9])[CH:15]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 8822734-(Pyridin-3-yloxy)-phthalonitrileYield 187.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-nitro-phthalonitrile (3.46 g, 20 mmol), pyridin-3-ol (1.90 g, 20 mmol), K2CO3 (8.29 g, 60 mmol), and DMF (50 ml) was stirred at ambient temperature overnight. The reaction mixture was then combined with another batch of the same reaction performed on the same scale. Subsequently, the solid components were removed by filtration and the filtrate was concentrated in vacuo. To the residue was added water and the mixture was extracted with EtOAc. The organic phase was then washed with brine, dried, and evaporated in vacuo. The residue was recrystallized from EtOAc/MeOH to give 8.3 g of the title compound; 1H NMR (CDCl3): δ=8.56 to 8.59 (m, 1H), 8.45 to 8.47 (m, 1H), 7.76 (d, 1H), 7.42 to 7.44 (m, 2 H), 7.22 to 7.32 (m, 2 H).

Workup

  1. customThe reaction mixture was then combined with another batch of the same reaction
  2. customSubsequently, the solid components were removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted with EtOAc
  6. washThe organic phase was then washed with brine
  7. customdried
  8. customevaporated in vacuo
  9. customThe residue was recrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-575fdcc0e9624b0881054d137c05b7c0
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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