Picolinic acid → Pyridine-2-carbonyl chloride
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.S(Cl)([Cl:12])=O.C(C1C=CC(N)=CC=1)#N.C(N(CC)CC)C.[OH-].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([Cl:12])=[O:9]Participants
Procedure
Picolinic acid chloride was prepared by refluxing a solution of picolinic acid (20.0 g, 162 mmol) and thionyl chloride (24.0 mL, 325 mmol) in chloroform (200 mL) overnight. After excess thionyl chloride and chloroform was removed in vacuo, some of the acid chloride (15.0 g, 106 mmol) was added to a solution of 4-cyanoaniline (10.0 g, 84.6 mmol) and triethylamine (30.0 mL, 215 mmol) in methylene chloride (250 mL) at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 1 hour, poured into water (1 L), basified with 2.5N sodium hydroxide solution, and diluted with methylene chloride. The organic layer was dried over magnesium sulfate and concentrated to give a light brown solid (8.22 g, 36.9 mmol, 44%, mp 156°-159° C.).
Workup
- customAfter excess thionyl chloride and chloroform was removed in vacuo
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7860ae0a220d4a599dafbdc43137eb03
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04873238
Reaction notes
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