Phosphorus oxychloride → 1-chloro-3-phenylisoquinoline
Reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Cl:19][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Phenylisoquinoline (5 g) was dissolved in dry toluene (250 ml) and phosphorus oxychloride (16.52 g) was added and the mixture was heated at reflux for 48 hr, more phosphorus oxychloride (4 g) being added after 24 hr. The solvent was removed in vacuo to give 1-chloro-3-phenylisoquinoline as an oil which solidified on standing (4 g), characterised by its nmr spectrum. (A small portion was recrystallised from methanol, m.pt. 75°-77°).