Thionyl Chloride → 5-Nitro-3-pyridinecarbonyl chloride
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9](O)=[O:10])([O-:3])=[O:2].S(Cl)([Cl:15])=O>>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([Cl:15])=[O:10])([O-:3])=[O:2]Participants
3
Procedure
A mixture of 2 g of 5-nitronicotinic acid and 30 ml. of thionyl chloride was refluxed for 3 hours. Excess thionyl chloride was distilled off to give oily 5-nitronicotinoyl chloride. The acid chloride thus obtained was added to 10 ml of pyridine at -15° C. and 1.4 g of 2-thiophene carboxamide was added thereto. The resulting mixture was stirred at room temperature for 16 hours. The solvent was distilled off under reduced pressure at a temperature below 40° C. and the residue was purified over silica gel chromatography and recrystallized from ethyl acetate-n-hexane to give 200 mg of the desired product. mp 187° C.
Workup
- distillationExcess thionyl chloride was distilled off
Sources & evidence
- ORD record
- ord-0e94bea58a6b4c4bbc07da8673a32e77
- Source dataset
- uspto-grants-1977_10
- Patent number
- US04053608
Reaction notes
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