Reaktion #76154

Reaktionsgleichung

4

2,4-Dichloro-alpha(ethoxymethylene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester

cyclopropylamine

→

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

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling below 10° C
2. 2
   Sonstigeevaporated to a dry mixture
3. 3
   workup.ADDITIONTo the dry mixture in dimethoxyethane (800 mL), a 60% sodium hydride-in-oil suspension (12.0 g) was added slowly
4. 4
   Temperaturwith cooling
5. 5
   workup.STIRRINGstirring
6. 6
   TemperaturThe mixture was heated at 80-85° C. for 3 h under nitrogen atmosphere
7. 7
   TemperaturIt was cooled
8. 8
   workup.ADDITIONwater (5 L) was added
9. 9
   Filtrationthe precipitate was filtered
10. 10
    Waschenwashed with water
11. 11
    Sonstigedried
12. 12
    workup.ADDITIONA solution of sodium hydroxide (20.0 g) in water (500 mL) was added
13. 13
    Temperaturthe mixture was refluxed for 2 h
14. 14
    TemperaturIt was cooled
15. 15
    Filtrationthe precipitate was filtered
16. 16
    WaschenThe solid was washed with water and acetone

Vorschrift

To a solution of 4 (80 g) in methylene chloride (800 mL), cyclopropylamine (44.0 g) was added with cooling below 10° C. The mixture was stirred at room temperature for 1 h and evaporated to a dry mixture. To the dry mixture in dimethoxyethane (800 mL), a 60% sodium hydride-in-oil suspension (12.0 g) was added slowly with cooling and stirring. The mixture was heated at 80-85° C. for 3 h under nitrogen atmosphere. It was cooled and water (5 L) was added and the precipitate was filtered and washed with water and dried. The ester was suspended in tetrahydrofuran (800 mL). A solution of sodium hydroxide (20.0 g) in water (500 mL) was added and the mixture was refluxed for 2 h. It was cooled and acidified with acetic acid and the precipitate was filtered. The solid was washed with water and acetone. wt=19.0 g of (7). m.p.=235-240° C.

Quelle