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

HRID 1914673Notes

Reaction equation

HRID 1914673 reaction equation
NC1C=C([O:8]C)C=CC=1CCCO.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][OH:25])=[C:18]([N+:26]([O-:28])=[O:27])[CH:17]=1>>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:8])=[O:25])=[C:18]([N+:26]([O-:28])=[O:27])[CH:17]=1

Participants

3

Reactant 2

HCID 593530083-(2-Amino-4-methoxyphenyl)propan-1-olHCID 593530583-(4-Methoxy-2-nitrophenyl)propan-1-ol

Product 1

HCID 241789753-(4-Methoxy-2-nitrophenyl)prop-2-enoic acid

Procedure

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.

Sources & evidence

ORD record
ord-f85eca40f2b5458daa50ea9184b3acc2
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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