Phosphorus oxychloride → HCID 86041352, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][C:7]([CH3:14])=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([CH3:14])[N:8]=1Participants
3
Procedure
A mixture of 6-methoxy-3-methyl-4-phenylisoquinolin-1(2H)-one (3.0 g) and 12 mL of POCl3 was heated to reflux for 1 h, then cooled to room temp and poured into ice. The mixture was extracted with EtOAc (3×). The combined organic solutions were washed with brine (1×) and saturated aqueous sodium carbonate (1×), then dried (Na2SO4) and concentrated. Flash chromatography (10% EtOAc/hexanes) gave 2.6 g of 1-chloro6-methoxy-3-methyl-4-phenylisoquinoline.
Workup
- temperaturewas heated
- temperatureto reflux for 1 h
- additionpoured into ice
- extractionThe mixture was extracted with EtOAc (3×)
- washThe combined organic solutions were washed with brine (1×) and saturated aqueous sodium carbonate (1×)