Trimethylsilyl iodide → 2-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

HRID 2106802Notes

Reaction equation

HRID 2106802 reaction equation
I[Si](C)(C)C.[C:6]([C:8]1[C:9]([O:18]C)=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)#[N:7]>C(Cl)(Cl)Cl>[C:6]([C:8]1[C:9]([OH:18])=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:13]=1)#[N:7]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 230489992-Methoxy-5-(trifluoromethyl)nicotinonitrile

Product 1

HCID 148370202-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Iodotrimethylsilane (6.2 ml, 0.044 mol) was added with stirring to a solution of 3.15 g (0.016 mol) of 3-cyano-2-methoxy-5-(trifluoromethyl)pyridine in 80 ml of chloroform under nitrogen and the mixture was allowed to stir at ambient temperature overnight. It was then concentrated by evaporation under reduced pressure and the residue partitioned between ether and 1N aqueous sodium hydroxide. The ethereal phase was extracted with more aqueous sodium hydroxide and the combined alkaline solutions were cooled and acidified with concentrated aqueous hydrochloric acid. The resulting mixture was extracted with ether several times and the combined ether extracts dried over sodium sulfate and concentrated by evaporation under reduced pressure. The residue was triturated with hot hexane, filtered, and dried to obtain 1.8 g (62 percent of theory) of the title compound as off-white crystals melting at 177-178.5° C. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. concentrationIt was then concentrated by evaporation under reduced pressure
  2. customthe residue partitioned between ether and 1N aqueous sodium hydroxide
  3. extractionThe ethereal phase was extracted with more aqueous sodium hydroxide
  4. temperaturethe combined alkaline solutions were cooled
  5. extractionThe resulting mixture was extracted with ether several times
  6. dry with materialthe combined ether extracts dried over sodium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue was triturated with hot hexane
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-6e19fdf9a62b484886877768df724f73
Source dataset
uspto-grants-1990_06
Patent number
US04931452

Reaction notes

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