Reaktion #68930

Reaktionsgleichung

4-methoxybenzylamine

2-bromo-4-chloro-5-nitropyridine

triethylamine

→

title compound

Ausbeute 77.2%

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

Ausbeute 77.2%

Lösungsmittel

acetonitrile

acetonitrile

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle