Reaktion #1797494

Reaktionsgleichung

5-(N-acetylamino)indane

p-iodotoluene

potassium carbonate

potassium hydroxide

→

indan-5-yl-p-tolylamine

Lösungsmittel

water

water

isoamyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwhile introducing a nitrogen gas
2. 2
   Sonstigehydrolysis at 130° C. for 2 hours
3. 3
   workup.ADDITIONwas added
4. 4
   SonstigeIsoamyl alcohol was removed by azeotropic distillation
5. 5
   workup.ADDITION200 ml of toluene was added
6. 6
   workup.DISSOLUTIONto dissolve the reaction product
7. 7
   FiltrationAfter filtration
8. 8
   FiltrationAfter filtering out the magnesium sulfate
9. 9
   Einengenthe filtrate was concentrated
10. 10
    Sonstigepurified with column chromatography (carrier: silica gel, elute: toluene:hexane=1:4)

Vorschrift

26.28 g (0.15 mol) of 5-(N-acetylamino)indane, 43.61 g (0.20 mol) of p-iodotoluene, 25.88 g (0.188 mol) of anhydrous potassium carbonate and 2.38 g (0.038 mol) of a copper powder were mixed and while introducing a nitrogen gas, the resulting mixture was heated to 20° C. and stirred for 6 hours. After completion of the reaction, 22.3 g of potassium hydroxide dissolved in 20 ml of water and 50 ml of isoamyl alcohol were added to conduct hydrolysis at 130° C. for 2 hours. After completion of the hydrolysis, 250 ml of water was added, and Isoamyl alcohol was removed by azeotropic distillation. 200 ml of toluene was added to dissolve the reaction product. After filtration, the reaction product was dehydrated with magnesium sulfate. After filtering out the magnesium sulfate, the filtrate was concentrated, and purified with column chromatography (carrier: silica gel, elute: toluene:hexane=1:4) to obtain 32.3 of indan-5-yl-p-tolylamine.

Quelle