Potassium Iodide → 3-ethyl-6-methyl-5-thiophen-2-yl-1H-pyridin-2-one

HRID 1921380Notes

Reaction equation

HRID 1921380 reaction equation
[CH2:1]([C:3]1[C:4]([O:15]C)=[N:5][C:6]([CH3:14])=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].[I-].[K+].C(#N)C.Cl[Si](C)(C)C>O>[CH2:1]([C:3]1[C:4](=[O:15])[NH:5][C:6]([CH3:14])=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 11673096HCID 11673096, compound

Product 1

HCID 674922683-ethyl-6-methyl-5-thiophen-2-yl-1H-pyridin-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-ethyl-2-methoxy-6-methyl-5-(thiophen-2-yl)pyridine (6.15 g, 26.36 mmol) of the above reaction, potassium iodide (8.75 g, 52.71 mmol) and acetonitrile (80 mL) is added chlorotrimethylsilane (6.69 mL, 52.71 mmol) and the resulting cloudy mixture is heated to 80° C. for 2 hr. The reaction is cooled, poured into water and the solids collected by filtration, washed with water, with ethyl acetate and dried giving 3-ethyl-6-methyl-5-(thiophen-2-yl)-1H-pyridin-2-one as a yellow solid (90% yield).

Workup

  1. temperatureThe reaction is cooled
  2. filtrationthe solids collected by filtration
  3. washwashed with water, with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-42de59cfb65848209e4f91f7849f0b89
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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