Reaction #985293

Reaction equation

7chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

DMSO

ethyleneglycol

KOtBu

→

1-Cyclopropyl-6-fluoro-7-(2-hydroxy-ethoxy)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Solvents

Water

Conditions

Workup

1. 1
   workup.ADDITIONwas added portionwise over 10 min
2. 2
   Temperaturethe temperature was increased to 105° C.
3. 3
   workup.WAITThe resulting solution was left in the refrigerator overnight
4. 4
   OtherThe precipitate obtained
5. 5
   Filtrationwas filtered
6. 6
   Washwashed with cold water
7. 7
   Otherdried
8. 8
   Otheraffording

Procedure

To a mixture of DMSO (5 ml) and ethyleneglycol (6 ml), KOtBu (1.6 g, 14.23 mmol) was added portionwise over 10 min, and then heated to 90° C. To the mixture, 7chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (1.0 g) was added portionwise over 20 min, the temperature was increased to 105° C. and the mixture was stirred for 6 h. Water (30 ml) was added to the reaction solution and the pH of the solution was adjusted to pH=5. The resulting solution was left in the refrigerator overnight. The precipitate obtained was filtered, washed with cold water, and dried affording a 2:1 mixture of Intermediate 26A and Intermediate 26B (1.0 g).

Source