Reaktion #72754

Reaktionsgleichung

N-(4-bromo-2-methoxy-6-nitrophenyl)acetamide

morpholine

BINAP

t-BuOK

→

desired product

Ausbeute 35.0%

N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide

Ausbeute 35.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed with N2
2. 2
   TemperaturIt was cooled to room temperature
3. 3
   Filtrationfiltered
4. 4
   EinengenThe filtrate was concentrated in-vacuo
5. 5
   SonstigeThe residue was purified by silica gel chromatography
6. 6
   Wascheneluted with MeOH/DCM=1/50

Vorschrift

A mixture of N-(4-bromo-2-methoxy-6-nitrophenyl)acetamide (2.89 g), morpholine (2.61 g), BINAP (1.21 g) and t-BuOK (1.53 g) in dioxane (50 mL) was degassed with N2 and the mixture was stirred at 110° C. in a sealed tube overnight. It was cooled to room temperature and filtered. The filtrate was concentrated in-vacuo. The residue was purified by silica gel chromatography eluted with MeOH/DCM=1/50 to afford the desired product (1.03 g, 35%) 1H NMR (300 MHz, CDCl3) δ ppm 2.15 (s, 1H), 3.18 (t, 4H, J=4.8 Hz), 3.85 (t, 4H, J=4.8 Hz), 3.88 (s, 3H), 6.63 (d, 1H, J=2.7 Hz), 6.96 (d, 1H, J=2.7 Hz).

Quelle