Iodine → 1-Phenyl-2-pyridin-4-ylethane-1,2-dione

HRID 271112Notes

Reaction equation

HRID 271112 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.[OH2:17].C([O-])([O-])=[O:19].[Na+].[Na+]>CS(C)=O>[C:1]1([C:7](=[O:19])[C:8]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 10340Sodium CarbonateHCID 3521724-(Phenylethynyl)pyridine

Product 1

HCID 2750111-Phenyl-2-pyridin-4-ylethane-1,2-dioneYield 30%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-(phenylethynyl)pyridine (2.25 g, 12.6 mmol) and powder iodine (1.60 g, 6.3 mmol) in DMSO (30 mL) is heated at 155° C. for 4 h. The reaction mixture is cooled and poured to H2O (100 mL). The aqueous is neutralized with powdered Na2CO3 to pH˜12 and extracted with EtOAc (2×100 mL). The combined organic extracts are washed sequentially with H2O (60 mL) and brine (60 mL), then dried and concentrated. The crude material is purified by chromatography (silica gel: EtOAc/hexane: 20/80) to afford the title compound (0.81 g, 30%) as an oil. MS (+) ES: 212 (M+H)+.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic extracts are washed sequentially with H2O (60 mL) and brine (60 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe crude material is purified by chromatography (silica gel: EtOAc/hexane: 20/80)

Sources & evidence

ORD record
ord-32057cbc368447d8ace7b862dde589a0
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

Loading…