Reacción #2333

Ecuación de reacción

4-chloropyridine hydrochloride

4-methoxyaniline

→

4-(4-pyridylamino)-methoxybenzene

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling the residue
2. 2
   Extracciónthe solution extracted with water (2×100 ml)
3. 3
   workup.ADDITIONThe aqueous extracts were treated with sodium hydroxide solution
4. 4
   Extracciónextracted with ethyl acetate (4×100 ml)
5. 5
   LavadoThe combined organic extracts were washed with water, and saturated sodium chloride solution
6. 6
   Otrodried
7. 7
   Otrothe solvent evaporated
8. 8
   OtroPurification by flash chromatography on silica
9. 9
   Lavadoeluting with 10% v/v methanol/dichloromethane

Procedimiento

A stirred mixture of 4-chloropyridine hydrochloride (2 g) and 4-methoxyaniline (4.9 g) was heated at 140° C. for 5 hours. After cooling the residue was dissolved in dichloromethane (250 ml), the solution extracted with water (2×100 ml). The aqueous extracts were treated with sodium hydroxide solution and then extracted with ethyl acetate (4×100 ml). The combined organic extracts were washed with water, and saturated sodium chloride solution, then dried and the solvent evaporated. Purification by flash chromatography on silica, eluting with 10% v/v methanol/dichloromethane gave 4-(4-pyridylamino)-methoxybenzene, 2 g, as a fawn solid: m.p. 159°-160° C.; NMR (d6DMSO) δ8.47 (1H, s), 8.09 (2H, d), 7.10 (2H, d), 6.92 (2H, d), 6.70 (2H, dd), 3.73 (3H, s); m/e 201 (M+H)+ ; calculated for C12H12 N2O3 : C, 72.0; H, 6.0; N, 14.0. found: C, 71.4; H, 6.1; N, 13.8%.

Fuente