Reaktion #481016

Reaktionsgleichung

3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-(4-nitrophenyl)-benzamide

hydrogen

→

white powder

Ausbeute 49.3%

3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-(4-aminophenyl)-benzamide

Ausbeute 49.3%

Lösungsmittel

ethanol dichloromethane

Pd/C

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter filtration on celite
2. 2
   Einengenthe filtrate is concentrated under vacuum
3. 3
   SonstigeThe precipitate formed
4. 4
   Filtrationis filtered
5. 5
   Waschenrinsed with 50 ml of diethyl ether
6. 6
   workup.ADDITIONThe amine is released from its salt by agitation in a mixture of 50 ml of ethyl acetate and 50 ml of 1M NaOH
7. 7
   SonstigeAfter decanting
8. 8
   Waschenthe organic phase is washed with 25 ml of 1M NaOH and 25 ml of brine
9. 9
   TrocknenThe organic solution is dried over sodium sulphate
10. 10
    Filtrationfiltered
11. 11
    Waschenrinsed
12. 12
    Einengenconcentrated to dryness under reduced pressure

Vorschrift

In a 250 ml Parr flask, 2.4 g (6.5 mmoles) of 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-(4-nitrophenyl)-benzamide is dissolved in 50 ml of an absolute ethanol/dichloromethane mixture (1/1) in the presence of 10% Pd/C. The mixture is agitated under 20 PSI of hydrogen, at 30° C., for one hour. After filtration on celite, the filtrate is concentrated under vacuum. The evaporation residue is taken up in 25 ml of a 1M HCl solution. The precipitate formed is filtered and rinsed with 50 ml of diethyl ether followed by 50 ml of ethyl acetate. The amine is released from its salt by agitation in a mixture of 50 ml of ethyl acetate and 50 ml of 1M NaOH. After decanting, the organic phase is washed with 25 ml of 1M NaOH and 25 ml of brine. The organic solution is dried over sodium sulphate, filtered, rinsed and concentrated to dryness under reduced pressure to produce 1.09 g (49%) of a white powder. Melting point: 220-221° C.

Quelle