Phosphorus oxychloride → 4-Chloro-7-methoxy-8-methylquinoline

Participants

Reaction Steps

A solution of 4-hydroxy-7-methoxy-8-methylquinoline (59, 6.4 g, 33.8 mmol) in POCl3 (17.2 g, 111.6 mmol) was heated at reflux for 1 h under nitrogen. Then, the resulting solution was cooled down to room temperature and the excess of POCl3 was evaporated under reduced pressure. The residue was partitioned between ice-cold 1N NaOH and AcOEt. The organic layer was dried (Na2SO4), and evaporated. The residue was purified by silica-gel filtration (AcOEt/CH2Cl2/Heptane, 4:4:2) to give 6.5 g (92.5%) of the target product 60 as yellow needles: m/z=208 (M+H)+.

Provenance & Evidence