2-Ethoxy-1-methoxy-4-nitro-benzene → 3-Ethoxy-4-methoxyaniline

Participants

Reaction Steps

Leave under hydrogen pressure (Patm) for 12 hours, 5 g of 2-ethoxy-1-methoxy-4-nitrobenzene (XIXaa), 500 mg of 10% palladium on charcoal (10% by weight of product to reduce), in 200 ml of methanol. Filter on celite, rinse several times with methanol. Evaporate to dryness. Take up in ether and evaporate. One obtains 3.28 g of the abovenamed product as a pinkish white powder. Yield: 79%. 1H-NMR (CDCl3, 300 MHz): d 1.46 (t, 3H, —CH3), 3.33 (s, 2H exchangeable, —NH2), 3.81 (s, 3H, OCH3), 4.05 (q, 2H, OCH2), 6.22(d, 1H Ar), 6.28 (dd, 1H Ar), 6.71 (d, 1H Ar).

Provenance & Evidence