Dimethyl Sulfoxide → 1-Cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Participants

Reaction Steps

A solution of 0.9 g (3.2 mmoles) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.7 g (6.4 mmoles) of 3-hydroxyazetidine, 1.6 g (16.0 mmoles) of triethylamine and 15 ml of DMSO is heated to 80° C. for 4 hours. It is allowed to cool, added to a mixture of ice and water, and adjusted to pH 5 giving a precipitate which is filtered and washed with water. The solid is dried under vacuum to yield 0.86 g (80%) of 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at 286°-288° C. Spectroscopic data are identical to those of method C.

Provenance & Evidence