Реакция #76154

Уравнение реакции

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

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Температураwith cooling below 10° C
2. 2
   Другоеevaporated 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
   Температураwith cooling
5. 5
   workup.STIRRINGstirring
6. 6
   ТемператураThe mixture was heated at 80-85° C. for 3 h under nitrogen atmosphere
7. 7
   ТемператураIt was cooled
8. 8
   workup.ADDITIONwater (5 L) was added
9. 9
   Фильтрацияthe precipitate was filtered
10. 10
    Промывкаwashed with water
11. 11
    Другоеdried
12. 12
    workup.ADDITIONA solution of sodium hydroxide (20.0 g) in water (500 mL) was added
13. 13
    Температураthe mixture was refluxed for 2 h
14. 14
    ТемператураIt was cooled
15. 15
    Фильтрацияthe precipitate was filtered
16. 16
    ПромывкаThe solid was washed with water and acetone

Методика

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.

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