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

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

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 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

temperaturerefluxed for 12 h
distillationAfterwards, the excess phosphorous oxychloride was distilled off
additionthe residue was poured into ice
temperaturecooled water
customthe precipitate that formed
filtrationwas filtered off

Sources & evidence

ORD record: ord-b309e95cbe9f4594af1d5931b4a3cb26
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040558B2

Reaction notes

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