反応 #452429

反応方程式

hydrochloric acid

hexane

4-(4-fluorobenzoyl)aminophenylhydrazine

5-phthalimidyl-2-pentanone

hydrochloric acid

→

product

収率 6.6%

N-[2-methyl-3-(2-phthalimidylethyl)-1H-indol-5-yl]-4-fluoro-benzamide

収率 6.6%

溶媒

ethanol

反応条件

後処理

1. 1
   温度heating
2. 2
   温度The reaction mixture was then cooled to 0° C.
3. 3
   その他The solid which formed
4. 4
   ろ過was filtered
5. 5
   洗浄washed with hexane
6. 6
   その他provided
7. 7
   その他after drying
8. 8
   濃縮The mother liquor was concentrated under reduced pressure
9. 9
   洗浄eluting with 1:1 hexane
10. 10
    workup.ADDITIONFractions containing product
11. 11
    濃縮concentrated under reduced pressure

実験手順

To a solution of 5.33 gm (21.7 mMol) 4-(4-fluorobenzoyl)aminophenylhydrazine and 5.03 gm (21.8 mMol) 5-phthalimidyl-2-pentanone in 100 mL ethanol were added 2 mL concentrated hydrochloric acid and the reaction mixture was heated at 80° C. for 14 hours. To the reaction mixture were then added an additional 3 mL concentrated hydrochloric acid and heating continued for an additional 6 hours. The reaction mixture was then cooled to 0° C. and 100 mL hexane were slowly added. The solid which formed was filtered and washed with hexane and provided, after drying, 6.67 gm of the desired compound. The mother liquor was concentrated under reduced pressure and then subjected to silica gel chromatography, eluting with 1:1 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide an additional 0.63 gm of product. Overall yield was 7.3 gm (76%).

出典