Hydrochloric Acid → 2-Azido-6-chloropyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[N:3]=1.Cl.[N:11]([O-])=O.[Na+]>O>[N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[N:3]=1)=[N+:9]=[N-:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Chloro-6-hydrazinopyridine (3.00 g, 20.90 mmol) was suspended in water (20 mL) and cooled to 0° C. Concentrated HCl (3.00 mL, 36.5 mmol) was added to dissolve the starting material and attain a pH of ˜1. Sodium nitrite (1.73 g, 25.07 mmol) in water (10 mL) was added dropwise. The thick suspension was allowed to warm to room temperature and extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and evaporated. The crude residue was purified by flash chromatography (0-10% EtOAc/hexanes) to afford the title compound as a colorless solid.
Workup
- dissolutionto dissolve the starting material
- temperatureto warm to room temperature
- extractionextracted with CH2Cl2 (2×)
- dry with materialThe combined organic layers were dried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe crude residue was purified by flash chromatography (0-10% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-18c8d642221240debf16412ecc5d6397
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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