Thionyl Chloride → 2,3-Dichloro-5-nitropyridine
Reaction equation
[Cl:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.S(Cl)([Cl:14])=O>>[Cl:14][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
3-Chloro-5-nitro-2-hydroxy-pyridine (20 g) was added in small portions to thionylchloride (200 mL) under vigorous stirring. The suspension was heated to 100° C. within 1 hour, stirred at 100° C. for 1 hour and then cooled to room temperature. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. The solution was washed with water (3×200 mL) and the organic layer was dried over MgSO4. The solvent was removed under reduced pressure to give 2,3-dichloro-5-nitropyridine (18 g) was obtained as a pale yellow solid.
Workup
- temperaturecooled to room temperature
- customThe solvent was removed under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate
- washThe solution was washed with water (3×200 mL)
- dry with materialthe organic layer was dried over MgSO4
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-0b46450f725f4245adaf0ef17817fd35
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299110B2
Reaction notes
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