Phosphorus oxychloride → 2-Chloro-6-ethylnicotinonitrile
Reaction equation
[C:1]([C:3]1[C:4](=O)[NH:5][C:6]([CH2:9][CH3:10])=[CH:7][CH:8]=1)#[N:2].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[C:6]([CH2:9][CH3:10])[N:5]=1Participants
Procedure
A mixture of 3-cyano-6-ethyl-2(1H)-pyridone (36.2 g, 0.24 mol) and phosphorus oxychloride (250 ml) was heated under reflux for 2 hours. The reaction solution was concentrated under a reduced pressure, and the resulting residue was mixed with toluene and concentrated under a reduced pressure. The thus obtained residue was diluted with chloroform and washed with 1 N sodium hydroxide aqueous solution. The aqueous layer was extracted with chloroform, and the chloroform layers were combined and dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-chloro-3-cyano-6-ethylpyridine (19.6 g, 49%) as an oily material.
Workup
- temperaturewas heated
- temperatureunder reflux for 2 hours
- concentrationThe reaction solution was concentrated under a reduced pressure
- additionthe resulting residue was mixed with toluene
- concentrationconcentrated under a reduced pressure
- additionThe thus obtained residue was diluted with chloroform
- washwashed with 1 N sodium hydroxide aqueous solution
- extractionThe aqueous layer was extracted with chloroform
- dry with materialdried over anhydrous magnesium sulfate
- customAfter removing magnesium sulfate
- filtrationby filtration
- concentrationthe filtrate was concentrated under a reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-1d884f5087eb4f6ead01179414288226
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06136810
Reaction notes
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