Phosphorus oxychloride → 2-Chloro-4-methyl-nicotinonitrile
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]=1Participants
3
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
- customTo a 250 mL flask equipped with a magnetic stirrer
- temperatureThe mixture was refluxed for one hour
- distillationThe excess POCl3 was distilled under reduced pressure
- additionThe residue was poured into water
- filtrationThe crystalline material was filtered
- customdried at
Sources & evidence
- ORD record
- ord-fd57edf38f1a444b84694a1ccd86f0ad
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06111112
Reaction notes
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