Phosphorus pentachloride → HCID 67125855, compound

HRID 243273Notes

Reaction equation

HRID 243273 reaction equation
CO[C:3]1[C:8]([C:9]#[N:10])=[C:7]([CH3:11])[N:6]=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:13]>P(Cl)(Cl)(Cl)=O>[Cl:13][C:3]1[C:8]([C:9]#[N:10])=[C:7]([CH3:11])[N:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 534026054-Methoxy-2-methylpyridine-3-carbonitrile

Product 1

HCID 67125855HCID 67125855, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To 4-methoxy-2-methylnicotinonitrile (Tet 6222, 2006) (100 mg, 0.67 mmol) in phosphoryl chloride (2 mL) was added phosphorus pentachloride (156 mg, 0.75 mmol). The mixture was heated to reflux under nitrogen for 15 h. The reaction was quenched with ice, stirred for 10 min, then neutralised with NaHCO3 and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), evaporated to dryness and purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane). Product containing fractions were evaporated to give the title compound as a pale pink solid, (35 mg, 34%). 1H NMR δ (ppm) (CDCl3-d): 8.56 (1H, d, J=5.46 Hz), 7.32 (2H, d, J=5.46 Hz), 2.81 (3H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for 15 h
  3. customThe reaction was quenched with ice
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated to dryness
  7. custompurified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane)
  8. additionProduct containing fractions
  9. customwere evaporated

Sources & evidence

ORD record
ord-3b650df287da4de9ae6dadfbde7bae5f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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