Phosphorus oxychloride → 8-Chloro-2-methyl-1,5-naphthyridine
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2O.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2Participants
3
Procedure
The suspension of 6-methyl-[1,5]naphthyridin-4-ol (1.60 g, 9.99 mmol) in POCl3 (25 mL) was heated under refluxing for 2 hrs. After cooling to room temperature, the reaction mixture was quenched with ice water and basified with NH4OH followed by extraction with AcOEt. The organic layer was washed with brine and dried over NaSO4, and concentrated to give 8-chloro-2-methyl-[1,5]naphthyridine as a brown solid (1.2 g, 67%). HR-MS-EI (+) m/e calcd for C9H7N2Cl (M+) 178.0298. found 178.0297.
Workup
- temperaturewas heated
- temperatureunder refluxing for 2 hrs
- customthe reaction mixture was quenched with ice water
- extractionfollowed by extraction with AcOEt
- washThe organic layer was washed with brine
- dry with materialdried over NaSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a158cea1f85541cea529233d3a545bfb
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07304074B2
Reaction notes
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