Reaktion #84027

Reaktionsgleichung

Hydrogen

Hydrogen

3-nitrophthalic acid

hydrogen

→

3-aminophthalic acid

Ausbeute 84.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was purged with nitrogen 3 times
2. 2
   FiltrationThe suspension was filtered through a celite bed
3. 3
   Waschenrinsed with methanol
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   Sonstigeisolated by vacuum filtration
6. 6
   SonstigeThe solid was dried in vacuo to a constant weight

Vorschrift

10% Pd/C (2.5 g), 3-nitrophthalic acid (75.0 g, 355 mmol) and ethanol (1.5 L) were charged to a 2.5 L Parr hydrogenator under a nitrogen atmosphere. Hydrogen was charged to the reaction vessel for up to 55 psi. The mixture was shaken for 13 hours, maintaining hydrogen pressure between 50 and 55 psi. Hydrogen was released and the mixture was purged with nitrogen 3 times. The suspension was filtered through a celite bed and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solid was reslurried in ether and isolated by vacuum filtration. The solid was dried in vacuo to a constant weight, affording 54 g (84% yield) of 3-aminophthalic acid as a yellow product. 1H-NMR (DMSO-d6) δ: 3.17 (s, 2H), 6.67 (d, 1H), 6.82 (d, 1H), 7.17 (t, 1H), 8-10 (br, s, 2H); 13C-NMR (DMSO-d6) δ: 112.00, 115.32, 118.20, 131.28, 135.86, 148.82, 169.15, 170.09.

Quelle