Phosphorus oxychloride → 2-Chloro-5,6-dimethylpyridine-3-carbonitrile

HRID 577797Notes

Reaction equation

HRID 577797 reaction equation
P(Cl)(Cl)([Cl:3])=O.O=[C:7]1[C:12]([C:13]#[N:14])=[CH:11][C:10]([CH3:15])=[C:9]([CH3:16])[NH:8]1>>[Cl:3][C:7]1[C:12]([C:13]#[N:14])=[CH:11][C:10]([CH3:15])=[C:9]([CH3:16])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 5905325,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 128911062-Chloro-5,6-dimethylpyridine-3-carbonitrileYield 66.7%

Procedure

Phosphorus oxychloride (15 mL) was added to 2-oxo-1,2-dihydro-5,6-dimethyl pyridine-3-carbonitrile (2.00 g, 13.5 mmol) in a two neck 50 mL round bottom flask, and this mixture was stirred at RT for 1 h, and then refluxed for 12 h. Afterwards, the excess phosphorous oxychloride was distilled off, and the residue was poured into ice cooled water. The aqueous solution was basified with saturated sodium bicarbonate solution, and the precipitate that formed was filtered off to afford the title compound (1.50 g), yield: 66.7%.

Workup

  1. temperaturerefluxed for 12 h
  2. distillationAfterwards, the excess phosphorous oxychloride was distilled off
  3. additionthe residue was poured into ice
  4. temperaturecooled water
  5. customthe precipitate that formed
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-b309e95cbe9f4594af1d5931b4a3cb26
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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