Réaction #10043

Équation de réaction

methyl-2-(methoxycarbonyl)-3-nitrobenzoate

hydrogen

→

product

Rendement 87.0%

Methyl-3-amino-2-(methoxycarbonyl)benzoate

Rendement 87.0%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   FiltrationThe mixture was filtered through Celite
2. 2
   Concentrationthe filtrate was concentrated in vacuo
3. 3
   Autreto yield an oil
4. 4
   AutreThe crude product was purified by flash chromatography (dichloromethane/ethyl acetate 95 to 5)

Mode opératoire

To a solution of methyl-2-(methoxycarbonyl)-3-nitrobenzoate (23.8 g, 99.51 mmol) in ethyl acetate (200 ml) was added 10% Pd/C (1.8 g). The mixture was hydrogenated under 50 psi of hydrogen for 3 hours in a Parr Type Shaker. The mixture was filtered through Celite and the filtrate was concentrated in vacuo to yield an oil. The crude product was purified by flash chromatography (dichloromethane/ethyl acetate 95 to 5) to afford 18.1 g (87%) of the product as a brown oil: 1H NMR (CDCl3) δ 7.22 (t, J=7.6 Hz, 1H), 6.90 (d, J=7.2 Hz, 1H), 6.79 (d, J=8.7 Hz), 5.07 (b, 2H), 3.85 (s, 3H), 3.83 (s, 3H).

Source