Phosphorus oxychloride → 6-Chloro-4-methylpyridine-2-carbonitrile

HRID 1476912Notes

Reaction equation

HRID 1476912 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N+:4]=1[O-])#[N:2].P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:5]1[N:4]=[C:3]([C:1]#[N:2])[CH:8]=[C:7]([CH3:9])[CH:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 37251652-Cyano-4-methylpyridin-1-ium-1-olate

Product 1

HCID 230023726-Chloro-4-methylpyridine-2-carbonitrileYield 81%

Procedure

A mixture of 2-cyano-4-methylpyridine-1-oxide (4.03 g, 30 mmol) in phosphoryl trichloride (80 mL, 858 mmol) was heated to reflux overnight. The solvent was removed in vacuo. The residue was treated with ice and its pH made basic using saturated NaOH solution at 0° C. The aqueous layer was extracted with DCM (3×). The organic layers were combined, dried over MgSO4, filtered, and evaporated in vacuo to give the title compound (3.7 g, 81%). ESI-MS m/z [M+H]+ 153.6.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed in vacuo
  4. additionThe residue was treated with ice and its pH
  5. customat 0° C
  6. extractionThe aqueous layer was extracted with DCM (3×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-10e84266e3324a50b006b0f931711cf6
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…