Sodium Iodide → 3-(5-Ethyl-2,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)benzonitrile

HRID 1921338Notes

Reaction equation

HRID 1921338 reaction equation
[CH2:1]([C:3]1[C:4]([CH3:20])=[C:5]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[C:6]([CH3:11])=[N:7][C:8]=1[O:9]C)[CH3:2].[I-].[Na+].Cl[Si](C)(C)C.C(#N)C>O>[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:11])=[C:5]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[C:4]=1[CH3:20])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 674922613-(5-Ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile

Product 1

HCID 116302223-(5-Ethyl-2,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)benzonitrileYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 3-(5-ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile (44 mg, 0.165 mmol), sodium iodide (50 mg, 0.33 mmol), chlorotrimethylsilane (58.4 μL, 0.33 mL) and acetonitrile (2 mL) is heated at reflux temperature for 3 hr. The cooled reaction mixture is diluted with water (10 mL) and extracted with dichloromethane. The extract is dried, filtered, concentrated and the residue is purified by chromatography eluting with cyclohexane-ethyl acetate then with dichloromethane-5% methanol. Product containing fractions are combined and concentrated to afford 3-(5-ethyl-2,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)benzonitrile (13 mg, 32%) as a beige solid. LC/MS: MS m/e=253 (M+H); RT 2.92 min.; 1H NMR (CDCl3, δ ppm) 7.69 (1H, d), 7.59 (1H, t), 7.45 (1H, s), 7.41 (1H, d), 2.63 (2H, q), 2.02 (3H, s), 1.84 (3H, s), 1.11 (3H, t).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hr
  3. customThe cooled reaction mixture
  4. extractionextracted with dichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue is purified by chromatography
  9. washeluting with cyclohexane-ethyl acetate
  10. additionProduct containing fractions
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-bd803979e21d40ed8fb05755fb5e6445
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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