Thionyl Chloride → 2-Chloropyridine-4-carbonyl chloride
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([Cl:13])=[O:6]Participants
Procedure
A mixture of 0.13 mol of 2-chloroisonicotinic acid and 70 ml of thionyl chloride is refluxed for 2 hours, then it is concentrated under reduced pressure and the residue is taken up with anhydrous toluene. The solvent is evaporated off and the crude 2-chloroisonicotinic acid chloride thus obtained in the form of a yellow solid is suspended in 50 ml of methylene chloride. The mixture is cooled to 0°-5° C. and a solution of 0.3 mol of piperidine in 50 ml of methylene chloride is added slowly thereto. The mixture is stirred two hours at room temperature, then washed thoroughly with water and the organic phase is evaporated to dryness. Thus, there is obtained 19 g of 2-chloro-4-piperidinocarbonylpyridine which is purified by chromatography on silica gel and elution with ethyl acetate. Thus, 10 g of a pure product in the form of a yellow oil are obtained.
Workup
- temperatureis refluxed for 2 hours
- concentrationit is concentrated under reduced pressure
- customThe solvent is evaporated off
Sources & evidence
- ORD record
- ord-47778b0059904816b2592301d21160f4
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04514408
Reaction notes
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