Reacción #68930

Ecuación de reacción

4-methoxybenzylamine

2-bromo-4-chloro-5-nitropyridine

triethylamine

→

title compound

Rendimiento 77.2%

N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine

Rendimiento 77.2%

Disolventes

acetonitrile

acetonitrile

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowas then washed successively with water and brine
2. 2
   Concentraciónbefore being concentrated in vacuo to a light brown oil which

Procedimiento

A solution of 4-methoxybenzylamine (0.756 g, 5.51 mmol) in acetonitrile (2 mL) was added to a mixture of 2-bromo-4-chloro-5-nitropyridine (1.19 g, 5.01 mmol) and triethylamine (0.768 mL, 5.51 mmol) in acetonitrile (8 mL). After stirring for 1.5 hours, the solution was diluted with ethyl acetate (100 mL) which was then washed successively with water and brine before being concentrated in vacuo to a light brown oil which solidified on standing to give the title compound (1.31 g, 3.87 mmol, 77%). 1H NMR (d6-DMSO, 400 MHz) δ 9.00 (br t, 1H, J=6.3 Hz), 8.80 (s, 1H), 7.35 (d, 2H, J=8.7 Hz), 7.10 (s, 1H), 6.95 (d, 2H, J=8.8 Hz), 4.60 (d, 2H, J=6.0 Hz), 3.70 (s, 3H). LCMS (1) Rt=2.13 min; m/z (ESI−) 336, 338 (M−H).

Fuente