Sodium Sulfide → (E)-3-(5-Amino-2-methoxy-phenyl)-N-methyl-acrylamide

Participants

Reaction Conditions

Reaction Steps

(E)-3-(5-Nitro-2-methoxy-phenyl)-N-methyl-acrylamide (0.75 g) and sodium sulphide (1.0 g) were combined in 1,4-dioxan/water (1:1, 20 ml) and warmed at 80° C. for 3 h. Solvent was removed at reduced pressure, the residue extracted with 10% methanol/dichloromethane and the extract filtered. The filtrate was evaporated to dryness and the residue column chromatographed (silica gel, 5% methanol:dichloromethane) to give the title compound (0.50 g). 1 H NMR δ: 2.68 (3H, d, J=0.4.8Hz), 3.71 (3H, s), 6.44 (1H, d, J=15.9 Hz), 6.60 (1H, dd, J=2.8 9.2 Hz), 6.73 (1H, d, J=2.8 Hz), 6.78 (1H, d, J=9.2 Hz), 7.57 (1H, d, J=15.9 Hz), 8.00 (1H, m).

Provenance & Evidence