Sodium Carbonate → 2-chloro-5-phenylnicotinonitrile

HRID 1593666Notes

Reaction equation

HRID 1593666 reaction equation
O=[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][NH:3]1.O=P(Cl)(Cl)[Cl:18].P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:18][C:2]1[N:3]=[CH:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 2970612-oxo-5-phenyl-1H-pyridine-3-carbonitrile

Product 1

HCID 27640432-chloro-5-phenylnicotinonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile (2.50 g, 12.7 mmol) was added to a suspension of POCl3 (1.5 ml) and PCl5 (7.35 g) at room temperature. The suspension was then stirred at reflux for 1 hour. The reaction mixture was cooled to room temperature and added cautiously to iced water. The solution was then adjusted to pH 11 with sodium carbonate and the resulting white solid was filtered, washed with water, then dried in vacuo to afford the title compound as a solid.

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationthe resulting white solid was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5550bfbf8b014d3b9ea184d4181d7e35
Source dataset
uspto-grants-2007_11
Patent number
US07297792B2

Reaction notes

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