Phosphorus oxychloride → 7-Chloro-3,5-dimethylisoxazolo[4,5-b]pyridine
Reaction equation
[CH3:1][C:2]1[C:6]2=[N+:7]([O-])[C:8]([CH3:11])=[CH:9][CH:10]=[C:5]2[O:4][N:3]=1.O=P(Cl)(Cl)[Cl:15].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:15][C:10]1[CH:9]=[C:8]([CH3:11])[N:7]=[C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
3,5-dimethylisoxazolo[4,5-b]pyridine 4-oxide (0.650 g, 3.96 mmol) in chloroform (5 mL), was added POCl3 (1.45 mL, 15.8 mmol) and the mixture was heated at 80° C. for 2 hours. The solution was cooled and poured onto ice water. The solution was neutralized with saturated NaHCO3 and the solution was then extracted with EtOAc, dried, and concentrated. The solid was triturated with ether and filtered twice to obtain two crops of the title compound (0.417 g, 57.7% yield).
Workup
- temperatureThe solution was cooled
- additionpoured onto ice water
- extractionthe solution was then extracted with EtOAc
- customdried
- concentrationconcentrated
- customThe solid was triturated with ether
- filtrationfiltered twice
Sources & evidence
- ORD record
- ord-ff9ef4ad650b41b7bee7f5e52f90b563
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354540B2
Reaction notes
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