Pyridine → 7-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

Participants

Reaction Steps

A suspension of 2 g (6.59 mmol) of 4-chloro-7-iodo-2-methylquinoline (EP497371) in ethanol (20 ml) was treated successively with 1.28 g (18.0 mmol) of pyrrolidine, pyridine (0.2 ml) and 50 mg (0.3 mmol) of potassium iodide and the resulting mixture was refluxed for 24 h. After concentration in vacuo, the residue was taken up in water (50 ml) and basified to pH 12 by addition of 2 M aq. sodium hydroxide solution. The precipitate was collected by filtration, washed with water (20 ml) and ether (20 ml) and dried to in a high vacuum to afford 1.95 g (87%) of 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline as off-white solid, m.p. 99-102° C.

Provenance & Evidence