N,N-Dimethylaniline → 4-Chlorobenzo[g]quinoline

Participants

Reaction Steps

Under a nitrogen atmosphere, benzo[g]quinolin-4-ol (6) (100 mg, 0.51 mmol) was refluxed in 2 ml of phosphorus oxychloride (0.25 M) in the presence of N,N-dimethylaniline (0.25 mL, 3.8 equivalents) until deemed complete by TLC. Removal of the excess phosphorus oxycloride in vacuo and flash chromatography (gradient: 9:1 to 8:2 to 7:3 hexanes:EtOAc) afforded 108 mg of clean 4-chlorobenzo[g]quinoline (7b) in quantitative yield.

Provenance & Evidence