Phosphorus oxychloride → 1,7-Dichloro-6-fluoroisoquinoline
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N+:8]([O-])=[CH:9]2)=[CH:4][C:3]=1[F:13].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:9]1[C:10]2[C:5](=[CH:4][C:3]([F:13])=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[CH:7][N:8]=1Participants
3
Procedure
2.6 g (12.0 mmol) of 7-Chloro-6-fluoro-isoquinoline 2-oxide (4) were heated in 40 ml of POCl3 at reflux for 4 h. After the mixture has cooled down to room temperature, it was poured on ice. The aqueous solution was extracted three times with dichloromethane. The combined organic layers were dried with MgSO4 and evaporated to yield 2.91 g of the title compound, which was used without further purification. Rt=2.34 min (Method A). Detected mass: 216.0/218.0 (M+H+).
Workup
- temperatureat reflux for 4 h
- additionit was poured on ice
- extractionThe aqueous solution was extracted three times with dichloromethane
- dry with materialThe combined organic layers were dried with MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-9cc687742f6840248303f47a2f99ad90
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461144B2
Reaction notes
Loading…