Reaction #2161231

Reaction equation

5-(N-acetylamino)indane

p-iodotoluene

potassium carbonate

potassium hydroxide

→

indan-5-yl-p-tolylamine

Solvents

water

water

Isoamyl alcohol

Conditions

Workup

1. 1
   workup.ADDITIONwhile introducing a nitrogen gas
2. 2
   Otherhydrolysis at 130° C. for 2 hours
3. 3
   workup.ADDITIONwas added
4. 4
   Otherisoamyl 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
   Concentrationthe filtrate was concentrated
10. 10
    Otherpurified with column chromatography (carrier:silica gel, elute:toluene:hexane=1:4)

Procedure

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 200° 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.

Source