反応 #76154

反応方程式

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

溶媒

methylene chloride

反応条件

後処理

1. 1
   温度with cooling below 10° C
2. 2
   その他evaporated 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
   温度with cooling
5. 5
   workup.STIRRINGstirring
6. 6
   温度The mixture was heated at 80-85° C. for 3 h under nitrogen atmosphere
7. 7
   温度It was cooled
8. 8
   workup.ADDITIONwater (5 L) was added
9. 9
   ろ過the precipitate was filtered
10. 10
    洗浄washed with water
11. 11
    その他dried
12. 12
    workup.ADDITIONA solution of sodium hydroxide (20.0 g) in water (500 mL) was added
13. 13
    温度the mixture was refluxed for 2 h
14. 14
    温度It was cooled
15. 15
    ろ過the precipitate was filtered
16. 16
    洗浄The solid was washed with water and acetone

実験手順

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.

出典