Reacción #452429

Ecuación de reacción

hydrochloric acid

hexane

4-(4-fluorobenzoyl)aminophenylhydrazine

5-phthalimidyl-2-pentanone

hydrochloric acid

→

product

Rendimiento 6.6%

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

Rendimiento 6.6%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheating
2. 2
   TemperaturaThe reaction mixture was then cooled to 0° C.
3. 3
   OtroThe solid which formed
4. 4
   Filtraciónwas filtered
5. 5
   Lavadowashed with hexane
6. 6
   Otroprovided
7. 7
   Otroafter drying
8. 8
   ConcentraciónThe mother liquor was concentrated under reduced pressure
9. 9
   Lavadoeluting with 1:1 hexane
10. 10
    workup.ADDITIONFractions containing product
11. 11
    Concentraciónconcentrated under reduced pressure

Procedimiento

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%).

Fuente