Reacción #59123

Ecuación de reacción

methyl 1-[2-(4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]cyclopentanecarboxylate

hydrochloric acid

→

methyl 1-[2-(4′-amino-1,1′-biphenyl-4-yl)-2-oxoethyl]cyclopentanecarboxylate

Rendimiento 80.8%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 100 mL flask fitted with a reflux condenser
2. 2
   TemperaturaUpon cooling
3. 3
   Filtraciónthe darkly-colored reaction mixture was filtered under reduced pressure through 2 cm Celite®/2 cm silica, in order
4. 4
   Otroto remove iron particulates and polar impurities
5. 5
   ConcentraciónThe yellow filtrate was concentrated under reduced pressure
6. 6
   Otroresulting in a solid
7. 7
   Otrothat was triturated with 20 mL diethyl ether/20 mL hexane

Procedimiento

To a 100 mL flask fitted with a reflux condenser was added methyl 1-[2-(4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]cyclopentanecarboxylate (1.68 g, 4.40 mmol) dissolved in 85% aqueous ethanol (55 mL), followed by addition of 2 N aqueous hydrochloric acid solution (2.20 mL) and finely powdered iron (0) (2.46 g, 44.1 mmol). The reaction mixture was heated to 85° C. over 2 h. Upon cooling, the darkly-colored reaction mixture was filtered under reduced pressure through 2 cm Celite®/2 cm silica, in order to remove iron particulates and polar impurities. The yellow filtrate was concentrated under reduced pressure, resulting in a solid that was triturated with 20 mL diethyl ether/20 mL hexane to afford methyl 1-[2-(4′-amino-1,1′-biphenyl-4-yl)-2-oxoethyl]cyclopentanecarboxylate as a light tan solid (1.20 g, 76%). LC-MS ret. time 2.71 min, m/z 338.1 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.55-1.84 (overlapping signals, 6H), 2.25-2.35 (m, 2H), 3.44 (s, 2H), 3.67 (s, 3H), 7.40-8.10 (overlapping signals, 8H).

Fuente