Dimethylformamide → 5-Chloro-2-cyanopyridine

HRID 1289760Notes

Reaction equation

HRID 1289760 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH3:9][N:10](C)C=O.[Cu](C#N)C#N.C(N(CC)CC)C>C(OCC)(=O)C.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]#[N:10])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8170982-Bromo-5-chloropyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 38339425-Chloro-2-cyanopyridineYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (10.0g) obtained in (1) above, dimethylformamide (50 ml), copper cyanide (6.98 g), triethylamine (10.9 ml) and molecular sieves 4A (2 g, heat-treated) were placed in an autoclave. The outer temperature was set for 200° C. and the mixture was stirred for 4 hours. Water and ethyl acetate were added to the reaction mixture, and, after filtering off insoluble matters, extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel column chromatography (hexane-ethyl acetate) to give 1.92 g of a white solid (yield 27%).

Workup

  1. customwas set for 200° C.
  2. filtrationafter filtering off insoluble matters
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-91a02675145e4e33aad73b7c70ccd80f
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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