Thionyl Chloride → 6-Cyanopyridine-3-carbonyl chloride
Reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][N:4]=1)#[N:2].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1.CN(C=O)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][N:4]=1)#[N:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
6-Cyano-nicotinic acid (120 mg, 810 μmol) was suspended in toluene (1 mL) and thionyl chloride (119 μL, 1.62 mmol) was added dropwise followed by one drop of DMF. The reaction mixture was refluxed for 2.5 hours and then allowed to cool to room temperature for 18 hours. The solvents were removed in vacuo and the residue was azeotroped with toluene to furnish the title compound as a brown oil (134 mg) which was used in further experiments without purification.
Workup
- temperatureThe reaction mixture was refluxed for 2.5 hours
- customThe solvents were removed in vacuo
- customthe residue was azeotroped with toluene
Sources & evidence
- ORD record
- ord-a0d68bfd70ad47b1bca584708294992a
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895544B2
Reaction notes
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