Thionyl Chloride → 2-Chloronicotinoyl chloride
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[S:11]([Cl:14])([Cl:13])=[O:12]>>[S:11]([Cl:14])([Cl:13])=[O:12].[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:13])=[O:5]Participants
4
Procedure
2-Chloro nicotinic acid (5 g, 31.8 mmol) was heated to reflux with redistilled thionyl chloride (5.6 g, 47 mmol) for 8 hr, resulting in a clear solution. The reaction mixture was concentrated to dryness and the traces of thionyl chloride co-distilled with toluene (15 ml) to give 2-chloro-nicotinoyl chloride (5.2 g, 94%) as oil.
Workup
- customresulting in a clear solution
- concentrationThe reaction mixture was concentrated to dryness
Sources & evidence
- ORD record
- ord-6ebf1a4168a4460eb2ae037327769b98
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486962B2
Reaction notes
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