Phosphorus oxychloride → 2-Chloro-4-methyl-nicotinonitrile

HRID 1873065Notes

Reaction equation

HRID 1873065 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428604HCID 178428604, compound

Product 1

HCID 123877362-Chloro-4-methyl-nicotinonitrileYield 89.2%

Procedure

To a 250 mL flask equipped with a magnetic stirrer was added 10 g of 2-hydroxy-4-methyl-3-pyridinylcarbonitrile (8) and 60 mL of phosphorous oxychloride. The mixture was refluxed for one hour. The excess POCl3 was distilled under reduced pressure. The residue was poured into water. The crystalline material was filtered and dried at to give 10.2 g (89.2%) of (9). m.p.: 109-110° C., NMR (DMSO); ppm: 2.56 (s,3H); 7.6 (bs,1H); 8.56 (m,1H).

Workup

  1. customTo a 250 mL flask equipped with a magnetic stirrer
  2. temperatureThe mixture was refluxed for one hour
  3. distillationThe excess POCl3 was distilled under reduced pressure
  4. additionThe residue was poured into water
  5. filtrationThe crystalline material was filtered
  6. customdried at

Sources & evidence

ORD record
ord-fd57edf38f1a444b84694a1ccd86f0ad
Source dataset
uspto-grants-2000_08
Patent number
US06111112

Reaction notes

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