Potassium Carbonate → 6-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

HRID 2060855Notes

Reaction equation

HRID 2060855 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.Cl[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 42818821-Chloro-4-hydroxyisoquinolineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 594013876-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-chloro-4-hydroxyisoquinoline (1.0 g, 5.6 mmol) in DMF (16 mL), was added 6-chloronicotinonitrile (0.55 g, 4.0 mmol) and K2CO3 (1.65 g, 11.9 mmol). The reaction mixture was heated at 70° C. for 6.5 h. Solvent was removed in vacuo and residue partitioned between EtOAc (100 mL), THF (100 mL) and water (60 mL). The organic phase was washed with water (2×60 mL), 1M NaOH (2×40 mL), brine (40 mL) and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=3.66 min; m/z (ES+)=282.0 [M+H]+.

Workup

  1. customSolvent was removed in vacuo and residue
  2. custompartitioned between EtOAc (100 mL), THF (100 mL) and water (60 mL)
  3. washThe organic phase was washed with water (2×60 mL), 1M NaOH (2×40 mL), brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-3c4ff8d0135045eaab7945089e091a7a
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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