Reacción #217897

Ecuación de reacción

water

4-(2-hydroxy-ethyl)-phenol

6-chloronicotinamide

K2CO3

→

title compound

Rendimiento 49.0%

6-[4-(2-Hydroxy-ethyl)-phenoxy]-nicotinamide

Rendimiento 49.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaCool to ambient temperature
2. 2
   Extracciónextract the aqueous layer with ethyl acetate
3. 3
   Secadodry over Na2SO4
4. 4
   Otropurify by flash chromatography on silica gel (eluent: CHCl3/7% EtOH/0.7% NH4OH)

Procedimiento

Combine 4-(2-hydroxy-ethyl)-phenol (2.0 g, 14.5 mmol), 6-chloronicotinamide (2.3 g, 14.5 mmol) and K2CO3 (5.0 g, 36.2 mmol) in DMF (40 mL) under nitrogen, stir and heat at 120° C. overnight. Cool to ambient temperature and pour into water, extract the aqueous layer with ethyl acetate. Combine the organic layers and dry over Na2SO4. Eliminate the solvent and purify by flash chromatography on silica gel (eluent: CHCl3/7% EtOH/0.7% NH4OH) to give the title compound (1.8 g, 49%). Electrospray MS M+1 ion=259, 1H-NMR (DMSO-d6, 400 MHz): 8.58 (d, 1H, J=2.7 Hz), 8.22 (dd, 1H, J=2.7 and 8.8 Hz), 8.00 (bs, 1H), 7.46 (bs, 1H), 7.25 (m, 2H), 7.05-7.02 (m, 3H), 4.65 (t, 1H), J=5.3 Hz), 3.63-3.58 (m, 2H), 2.72 (t, 2H, J=6.9 Hz).

Fuente