Phosphorus pentachloride → 6-chloro-5-nitronicotinonitrile

HRID 1370119Notes

Reaction equation

HRID 1370119 reaction equation
O[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:15]>P(Cl)(Cl)(Cl)=O>[Cl:15][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]#[N:8])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178513756HCID 178513756, compound

Product 1

HCID 185096266-chloro-5-nitronicotinonitrileYield 108.8%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-hydroxy-5-nitronicotinamide (343 g), phosphorus oxychloride (40 ml) and phosphorus pentachloride (1287 g) was heated at 130° C. for 3.5 hours. After cooling to ambient temperature, the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and an aqueous saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and evaporated to afford 6-chloro-5-nitronicotinonitrile (374 g) as an oil.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c1566577dfda4a5490cc50ad67a4dd21
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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