Reaktion #1447127

Reaktionsgleichung

anthranilonitrile

magnesium

isobutylmagnesium bromide

tetrahydrofuran

tetrahydrofuran

hydrochloric acid

→

1-(2-aminophenyl)-3-methylbutan-1-one

Ausbeute 25.0%

Lösungsmittel

water

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAt reflux
2. 2
   TemperaturAfter 5 h of heating
3. 3
   Temperaturunder reflux
4. 4
   Sonstigeare, at 0° C.
5. 5
   workup.ADDITIONadded to the reaction mixture
6. 6
   WaschenThe organic phase is washed with water
7. 7
   Trocknendried over magnesium sulphate
8. 8
   EinengenConcentration
9. 9
   Sonstigeunder reduced pressure and purification on silica gel (mobile phase: petroleum ether/acetonitrile 95:5)

Vorschrift

At reflux, a solution of 29.5 g (0.25 mol) of anthranilonitrile in 150 ml of tetrahydrofuran is added dropwise to a suspension comprising 18.2 g (0.75 mmol) of magnesium, 375 ml of a 2 M solution of isobutylmagnesium bromide in tetrahydrofuran and 15 ml of diethyl ether. After 5 h of heating under reflux, 100 ml of water are, at 0° C., added to the reaction mixture, and the pH is adjusted to 6 using hydrochloric acid. The organic phase is washed with water and dried over magnesium sulphate. Concentration under reduced pressure and purification on silica gel (mobile phase: petroleum ether/acetonitrile 95:5) gives 11.0 g (25% of theory) of 1-(2-aminophenyl)-3-methylbutan-1-one of logP (pH 2.3)=2.89.

Quelle