Reaction #985294

Reaction equation

ethanolamine

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

MeOH

→

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

Solvents

N-methyl pyrrolidinone

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to about 60° C.
2. 2
   workup.STIRRINGThis mixture was stirred in an ice bath
3. 3
   Filtrationthe precipitate was filtered off
4. 4
   Otherdried
5. 5
   Otheraffording

Procedure

To a solution of ethanolamine (55.5 ml) in N-methyl pyrrolidinone (500 ml) at 95° C., 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (50.0 g) was slowly added under vigorous stirring. The temperature was increased to 105° C. and the reaction mixture was stirred at this temperature for 22 hours. The reaction mixture was cooled to about 60° C. and poured into MeOH (800 ml). This mixture was stirred in an ice bath and the precipitate was filtered off and dried affording a mixture of Intermediate 29A and Intermediate 29B (49 g ) in a 1:1 ratio.

Source