Potassium Cyanide → [7-Fluoro-2-(methyloxy)-8-quinolinyl]acetonitrile

HRID 1916306Notes

Reaction equation

HRID 1916306 reaction equation
Br[CH2:2][C:3]1[C:4]([F:15])=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2.[C-:16]#[N:17].[K+]>CN(C=O)C>[F:15][C:4]1[C:3]([CH2:2][C:16]#[N:17])=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 667376508-(Bromomethyl)-7-fluoro-2-(methyloxy)quinoline

Product 1

HCID 67130956[7-Fluoro-2-(methyloxy)-8-quinolinyl]acetonitrileYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8-bromomethyl-7-fluoro-2-methoxy-quinoline (20.0 g, 74 mmol; prepared as in WO 2007/081597) in DMF (530 mL) was added KCN (22.1 g, 339 mmol) and the mixture was stirred at 70° C. overnight. The mixture was concentrated, water and EA were added and the aq. layer was extracted with EA. The combined org layers were washed with brine, dried over MgSO4 and concentrated to afford the title intermediate as a beige solid (16.13 g, 100% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater and EA were added
  3. extractionthe aq. layer was extracted with EA
  4. washThe combined org layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a62d0afbb6674d8dbdfe33d2a44996be
Source dataset
uspto-grants-2013_12
Patent number
US08618092B2

Reaction notes

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