반응 #76154

반응 방정식

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

용매

methylene chloride

반응 조건

후처리

1. 1
   온도with cooling below 10° C
2. 2
   기타evaporated 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
   온도with cooling
5. 5
   workup.STIRRINGstirring
6. 6
   온도The mixture was heated at 80-85° C. for 3 h under nitrogen atmosphere
7. 7
   온도It was cooled
8. 8
   workup.ADDITIONwater (5 L) was added
9. 9
   여과the precipitate was filtered
10. 10
    세척washed with water
11. 11
    기타dried
12. 12
    workup.ADDITIONA solution of sodium hydroxide (20.0 g) in water (500 mL) was added
13. 13
    온도the mixture was refluxed for 2 h
14. 14
    온도It was cooled
15. 15
    여과the precipitate was filtered
16. 16
    세척The solid was washed with water and acetone

실험 절차

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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