Dimethylformamide → 2-(2-Fluoropyridin-4-YL)acetonitrile

HRID 2275261Notes

Reaction equation

HRID 2275261 reaction equation
[CH3:1][N:2](C=O)C.[F:6][C:7]1[CH:12]=[C:11]([CH2:13]OS(C)(=O)=O)[CH:10]=[CH:9][N:8]=1.[C-]#N.[Na+]>C(OCC)(=O)C>[F:6][C:7]1[CH:12]=[C:11]([CH2:13][C:1]#[N:2])[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 10488448(2-Fluoropyridin-4-yl)methyl methanesulfonate

Product 1

HCID 552673432-(2-Fluoropyridin-4-YL)acetonitrileYield 36%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To the DMF (28 ml) solution of methanesulfonic acid (2-fluoropyridin-4-yl)methyl ester (1.16 g), sodium cyanide (0.42 g) was added and the mixture was stirred at 80° C. for 1 hr. The mixture was diluted with ethyl acetate (100 ml), and washed with 15% brine and distilled water in order. The organic layer was concentrated and purified by silica gel column (n-hexane/ethyl acetate=5/1) to obtain the title compound (278 mg, 36%).

Workup

  1. washwashed with 15% brine
  2. distillationdistilled water in order
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel column (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-4d787c20327248ff8feb639e7459480d
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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