Dimethylformamide → HCID 90190361, compound

HRID 59959Notes

Reaction equation

HRID 59959 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cu]([C:11]#[N:12])C#N.CC[O:15]C(C)=O.[OH2:19].[CH3:20][N:21](C=O)C>>[CH3:5][C:6]1[CH:7]=[CH:2][N:3]=[C:4]([C:20]#[N:21])[C:11]=1[N+:12]([O-:15])=[O:19]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79732-BromopyridineHCID 22728543Water ethylacetateHCID 178418260HCID 178418260, compound

Product 1

HCID 90190361HCID 90190361, compoundYield 63.7%

Procedure

The bromopyridine (110 g, 0.51 mol) and freshly prepared copper cyanide (50 g, 0.56 mol) were heated in DMF (1 L) at 100° C. for 13 hours. The reaction mixture was allowed to cool to room temperature and poured into a mixture EtOAc/H2O (1.5 L: 3 L). Obtained triphasic mixture was filtered from inorganic solid material. Organic phase was separated, washed with water and dried over sodium sulfate. The solvent was evaporated to provide the title compound (yield 63.7%).

Workup

  1. customObtained triphasic mixture
  2. filtrationwas filtered from inorganic solid material
  3. customOrganic phase was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c3c4908f6c224dbab42a50458044a34d
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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