Реакция #318835

Уравнение реакции

5-fluoro-2,3-indolinedione

sodium hydroxide

acetoxyacetylbiphenyl

ethanol

→

desired product

6-Fluoro-3-hydroxy-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

Растворители

water

water

Условия реакции

Обработка

1. 1
   Другоеto provide solution
2. 2
   ТемператураThe mixture was refluxed for 3 hours
3. 3
   workup.DISTILLATIONDuring the last 1/2 hour 10 ml of ethanol was distilled off
4. 4
   workup.ADDITIONA 103 ml portion of water was added
5. 5
   Температураcooled
6. 6
   Фильтрацияfiltered through diatomaceous earth
7. 7
   workup.ADDITIONThe filtrate was treated with 13.6 ml of concentrated hydrochloric acid and 4.39 ml of glacial acetic acid
8. 8
   workup.STIRRINGstirred for 30 minutes
9. 9
   ДругоеThe resulting precipitate was collected
10. 10
    Промывкаwashed with water and ether and air
11. 11
    Другоеdried
12. 12
    workup.STIRRINGThe resulting solid was stirred
13. 13
    Температураheated in 400 ml of ethanol
14. 14
    ДругоеThe solid was collected
15. 15
    Промывкаwashed with water
16. 16
    Другоеdried

Методика

A suspension of 6.6 g of 5-fluoro-2,3-indolinedione in 48 ml of water was treated with a sufficient amount of a solution of 6.62 g of sodium hydroxide in 22 ml of water to provide solution. A warm solution of 10.17 g of acetoxyacetylbiphenyl in 80 ml of ethanol was added, followed by the balance of the alkali solution. The mixture was refluxed for 3 hours. During the last 1/2 hour 10 ml of ethanol was distilled off. A 103 ml portion of water was added, the mixture was stirred, cooled and filtered through diatomaceous earth. The filtrate was treated with 13.6 ml of concentrated hydrochloric acid and 4.39 ml of glacial acetic acid and stirred for 30 minutes. The resulting precipitate was collected, washed with water and ether and air dried. The resulting solid was stirred and heated in 400 ml of ethanol. The solid was collected, washed with water and dried giving 11.2 g of the desired product, mp 25220 -254° C.

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