Potassium Cyanide → 3,4-dihydro-2H-pyrano[2,3-b]pyridine-4-carbonitrile

HRID 1481325Notes

Reaction equation

HRID 1481325 reaction equation
Cl[CH:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[C-:12]#[N:13].[K+]>CN(C=O)C.[OH-].[Na+]>[O:5]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:11]2[CH:2]([C:12]#[N:13])[CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 1178190694-chloro-3,4-dihydro-2H-pyrano[2,3-b]pyridine

Product 1

HCID 897048393,4-dihydro-2H-pyrano[2,3-b]pyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-chloro-3,4-dihydro-2H-pyrano[2,3-b]pyridine (18.7 mmol) in 60 mL DMF was added KCN (56.1 mmol) and the mixture was stirred at 90° C. overnight. After cooling to RT, the mixture was diluted with aq. 0.5 M NaOH solution and extracted 3 times with EtOAc. The combined organic layers were washed again with aq. 0.5 M NaOH solution and once with brine. The organic phase was dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept/EtOAc (4/1) to EtOAc gives the desired compound as yellow oil.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted 3 times with EtOAc
  3. washThe combined organic layers were washed again with aq. 0.5 M NaOH solution and once with brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-9be1c10f0758443c99115bf836d49912
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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