Reaktion #64077

Reaktionsgleichung

ammonium hydroxide

hydrochloric acid

p-nitrophenethylamine

cis-1,2,3,6-tetrahydrophthalic anhydride

ammonium hydroxide

→

4-(cis-1,2,3,6-tetrahydrophthalimidoethyl) aniline

4-(cis-1,2,3,6-tetrahydrophthalimidoethyl)aniline

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture is cooled
2. 2
   Temperaturby warming under reduced pressure
3. 3
   SonstigeThe residue is transferred to a flask
4. 4
   Sonstigereaches 90° C.
5. 5
   workup.STIRRINGContinue stirring
6. 6
   Temperaturheating during the additions
7. 7
   workup.WAITThe total reaction time is 8-10 minutes
8. 8
   FiltrationThe solid is collected by filtration
9. 9
   Waschenwashed with water
10. 10
    SonstigeRecrystallize from water ethanol

Vorschrift

16.6 g of p-nitrophenethylamine and 15.1 g of cis-1,2,3,6-tetrahydrophthalic anhydride are heated under reflux in 300 ml of toluene, with stirring and a water trap, for 16 hours. This mixture is cooled and take to dryness by warming under reduced pressure. The residue is transferred to a flask containing 500 ml of water, 270 g ferrous sulfate heptahydrate and 1.3 ml concentrated hydrochloric acid. Steam is delivered to the mixture. When the temperature reaches 90° C., 75 ml of concentrated ammonium hydroxide is added in one portion, and at two-minute intervals three 25 ml portions of ammonium hydroxide are added. Continue stirring and heating during the additions. The total reaction time is 8-10 minutes. Immediately pour the mixture onto 1 kg of cracked ice. The solid is collected by filtration and washed with water. Recrystallize from water ethanol to obtain -4-(cis-1,2,3,6-tetrahydrophthalimidoethyl) aniline (1f).

Quelle