3-(2-Amino-4-methoxyphenyl)propan-1-ol → 3-(4-Methoxy-2-nitrophenyl)prop-2-enoic acid

Participants

Reaction Steps

In particular, 3-(2-amino-4-methoxyphenyl)propan-1-ol may be prepared by hydrogenation of 3-(4-methoxy-2-nitrophenyl)propan-1-ol obtained by reduction of (2E)-3-(4-methoxy-2-nitrophenyl)acrylic acid, resulting from the condensation of malonic acid with 4-methoxy-2-nitrobenzaldehyde. The latter may prepared by hydrolysis of 1-(dibromomethyl)-4-methoxy-2-nitrobenzene obtained by dibromination of 4-methyl 3-nitroanisole. Similarly, 2-[3-(dimethylamino)propyl]-5-methoxyaniline may be prepared by hydrogenation of the product resulting from the reaction between dimethyl amine and 3-(4-methoxy-2-nitrophertyl)propyl methanesulfonate. The latter may be obtained by methanesulfonylation of 3-(4-methoxy-2-nitrophenyl)propan-1-ol as described in the scheme below.

Provenance & Evidence