Picolinic acid → Pyridine-2-carbonyl azide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N(CC)CC)C.C(OC(Cl)=O)C.[N-:23]=[N+:24]=[N-:25].[Na+]>CC(C)=O.O>[N:23]([C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9])=[N+:24]=[N-:25]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of picolinic acid (1.0 g, 8.12 mmol) in a mixture of acetone (10 mL) and water (3 mL) was added triethylamine (1.7 mL, 12.2 mmol). The mixture was cooled to 0° C. in a ice-bath. Ethylchloroformate (1.32 g, 12.2 mmol) was then added and the resulting mixture was stirred for 1.5 hours at 0° C. To the mixture was added sodium azide (0.844 g, 13.0 mmol), and the mixture was stirred for another 1.5 hours. The mixture was concentrated, the residue was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4 and concentrated to give desired product (817 mg, 68%). 1HNMR (CDCl3) (δ) 8.74 (d, 1H), 8.15 (d, 1H), 7.88 (m, 1H), 7.55 (m, 1H).
Workup
- stirringthe mixture was stirred for another 1.5 hours
- concentrationThe mixture was concentrated
- additionthe residue was diluted with dichloromethane
- washwashed with water
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6c6a17e4df4c4e08bc41cce23ac0fa8c
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06608077B2
Reaction notes
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