Dimethylformamide → HCID 67291544, compound

HRID 1685400Notes

Reaction equation

HRID 1685400 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:9])=[CH:4][CH:3]=1.C(OCC)(=O)C.[CH3:23][N:24](C)C=O>O.Cl>[OH:16][C:15]1[C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:23]#[N:24])=[CH:3][CH:4]=2)=[O:9])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 67292422HCID 67292422, compound

Product 1

HCID 67291544HCID 67291544, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

10 g (35.96 mM) of (4-bromophenyl)(3-hydroxy-2-pyridinyl)methanone are mixed with 6.44 g (71.92 mM) of cuprous cyanide in 90 ml of dimethylformamide. The mixture is refluxed for 21 h. A solution of 19.25 g of ferric chloride in 42.5 ml of water and 6.7 ml of concentrated hydrochloric acid is prepared and added to the cooled reaction medium and the resulting mixture is then heated at 90° C. for 30 minutes. After cooling, ethyl acetate and water are added and the mixture is filtered on Celite. The product is then extracted with ethyl acetate and the organic phase is washed with saturated sodium chloride solution. The solvent is evaporated off under reduced pressure to give the desired product in the form of a yellow solid with a yield of 45%.

Workup

  1. temperatureThe mixture is refluxed for 21 h
  2. additionadded to the cooled reaction medium
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered on Celite
  5. extractionThe product is then extracted with ethyl acetate
  6. washthe organic phase is washed with saturated sodium chloride solution
  7. customThe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b1e785ae339b415aa1d783394eb3cae5
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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